Stereoselective Total Synthesis
of (3R,5R)-5-Hydroxy-de-O-methyllasiodiplodin via the Prins Cyclization

Jhillu S. Yadav; N. Thrimurtulu; Md. Ataur Rahman; J. Satyanarayana Reddy; A. R. Prasad; B. V. Subba Reddy

doi:10.1055/s-0030-1258244

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2010(21): 3657-3662
DOI: 10.1055/s-0030-1258244

PAPER

Stereoselective Total Synthesis of (3R,5R)-5-Hydroxy-de-O-methyllasiodiplodin via the Prins Cyclization

Jhillu S. Yadav*, N. Thrimurtulu, Md. Ataur Rahman, J. Satyanarayana Reddy, A. R. Prasad, B. V. Subba Reddy
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;

Further Information

Publication History

Received 5 July 2010
Publication Date:
07 September 2010 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

A practical stereoselective total synthesis of (3R,5R)-5-hydroxy-de-O-methyllasiodiplodin has been accomplished via Prins cyclization. It exhibits potato microtuber inducing activity. The synthetic sequence involves Prins cyclization, reductive opening of the pyran ring, esterification, and ring-closing metathesis (RCM) as the key steps.

Key words

Prins cyclization - ring-closing metathesis - esterification - reductive ring opening - lactone

References

1a Yang Q. Asai M. Matsuura H. Yoshihara T. Phytochemistry 2000, 54: 489

Google Scholar
1b Matsuura H. Nakamori K. Omer EA. Hatakeyama C. Yoshihara T. Ichihara A. Phytochemistry 1998, 49: 579

Google Scholar
1c Nakamori K. Matsuura H. Yoshihara T. Ichihara A. Koda Y. Phytochemistry 1994, 35: 835

Google Scholar
2a Uin M. Lett R. Lampilas M. Tischkowsky I. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products Vol. 2: Springer; Berlin: 1993. p.99

Google Scholar
2b Yadav JS. Das S. Reddy JS. Thrimurtulu N. Prasad AR. Tetrahedron Lett. 2010, 51: 4050

Google Scholar
3a Stob M. Baldwin RS. Tuite J. Andrews FN. Gillette KG. Nature 1962, 196: 1318

Google Scholar
3b Keinan E. Sinha SC. Sinha-Bagchi A. J. Chem. Soc., Perkin Trans. 1 1991, 3333

Google Scholar
4a Gerlach H. Helv. Chim. Acta 1977, 60: 3039

Google Scholar
4b Oyama H. Sassa T. Ikeda M. Agric. Biol. Chem. 1978, 42: 2407

Google Scholar
4c Yang R. Li Ch. Lin Y. Peng G. She Z. Zhou S.-H. Bioorg. Med. Chem. Lett. 2006, 16: 4205

Google Scholar
5 Bonini C. Chiummiento L. Lopardo MT. Pullex M. Colobert F. Solladie G. Tetrahedron Lett. 2003, 44: 2695

Crossref Google Scholar
6 Furrow ME. Schaus SE. Jacobsen EN. J. Org. Chem. 1998, 63: 6776

Google Scholar
For the Prins cyclization, see for example:
7a Barry CSt. J. Crosby SR. Harding JR. Hughes RA. King CD. Parker GD. Willis CL. Org. Lett. 2003, 5: 2429

Google Scholar
7b Yang X.-F. Mague JT. Li C.-J. J. Org. Chem. 2001, 66: 739

Google Scholar
7c Aubele DL. Wan S. Floreancig PE. Angew. Chem. Int. Ed. 2005, 44: 3485

Google Scholar
7d Barry CS. Bushby N. Harding JR. Willis CS. Org. Lett. 2005, 7: 2683

Google Scholar
7e Cossey KN. Funk RL. J. Am. Chem. Soc. 2004, 126: 12216

Google Scholar
7f Crosby SR. Harding JR. King CD. Parker GD. Willis CL. Org. Lett. 2002, 4: 3407

Google Scholar
7g Marumoto S. Jaber JJ. Vitale JP. Rychnovsky SD. Org. Lett. 2002, 4: 3919

Google Scholar
7h Kozmin SA. Org. Lett. 2001, 3: 755

Google Scholar
7i Jaber JJ. Mitsui K. Rychnovsky SD. J. Org. Chem. 2001, 66: 4679

Google Scholar
7j Kopecky DJ. Rychnovsky SD. J. Am. Chem. Soc. 2001, 123: 8420

Google Scholar
7k Rychnovsky SD. Thomas CR. Org. Lett. 2000, 2: 1217

Google Scholar
7l Rychnovsky SD. Yang G. Hu Y. Khire UR. J. Org. Chem. 1997, 62: 3022

Google Scholar
7m Su Q. Panek JS. J. Am. Chem. Soc. 2004, 126: 2425

Google Scholar
7n Yadav JS. Reddy BVS. Sekhar KC. Gunasekar D. Synthesis 2001, 885

Google Scholar
7o Yadav JS. Reddy BVS. Reddy MS. Niranjan N. J. Mol. Catal. A: Chem. 2004, 210: 99

Google Scholar
7p Yadav JS. Reddy BVS. Reddy MS. Niranjan N. Prasad AR. Eur. J. Org. Chem. 2003, 1779

Google Scholar
8a Yadav JS. Reddy MS. Rao PP. Prasad AR. Tetrahedron Lett. 2006, 47: 4397

Google Scholar
8b Yadav JS. Reddy MS. Prasad AR. Tetrahedron Lett. 2006, 47: 4937

Google Scholar
8c Yadav JS. Reddy MS. Prasad AR. Tetrahedron Lett. 2005, 46: 2133

Google Scholar
8d Yadav JS. Reddy MS. Prasad AR. Tetrahedron Lett. 2006, 47: 4995

Google Scholar
8e Yadav JS. Reddy MS. Rao PP. Prasad AR. Synlett 2007, 2049

Google Scholar
8f Yadav JS. Rao PP. Reddy MS. Rao NV. Prasad AR. Tetrahedron Lett. 2007, 48: 1469

Google Scholar
8g Yadav JS. Kumar NN. Reddy MS. Prasad AR. Tetrahedron 2007, 63: 2689

Google Scholar
8h Rao AVR. Reddy ER. Joshi BV. Yadav JS. Tetrahedron Lett. 1987, 28: 6497

Google Scholar
8i Yadav JS. Thrimurtulu N. Uma Gayathri K. Reddy BVS. Prasad AR. Tetrahedron Lett. 2008, 49: 6617

Google Scholar
8j Yadav JS. Thrimurtulu N. Venkatesh M. Raghavendra Rao KV. Prasad AR. Reddy BVS. Synthesis 2010, 73

Google Scholar
8k Yadav JS. Reddy NM. Reddy PA. Ather H. Prasad AR. Synthesis 2010, 1473

Google Scholar
8l Yadav JS. Ather H. Rao NV. Reddy MS. Prasad AR. Synlett 2010, 1205

Google Scholar
8m Sabitha G. Prasad MN. Shankaraiah K. Yadav JS. Synthesis 2010, 1171

Google Scholar
8n Yadav JS. Ather H. Gayathri KU. Rao NV. Prasad AR. Synthesis 2008, 3945

Google Scholar
8o Yadav JS. Thrimurtulu N. Venkatesh M. Prasad AR. Synthesis 2010, 431

Google Scholar
8p Yadav JS. Venkatesh M. Thrimurtulu N. Prasad AR. Synlett 2010, 1255

Google Scholar
9a Yadav JS. Reddy MS. Prasad AR. Tetrahedron Lett. 2005, 46: 2133

Google Scholar
9b Yadav JS. Lakshmi KA. Reddy NM. Prasad AR. Reddy BVS. Tetrahedron 2010, 66: 334

Google Scholar
10a Bhattacharjee A. De Brabander JK. Tetrahedron Lett. 2000, 41: 8069

Google Scholar
10b Nicolaou KC. Kim DW. Baati R. Angew. Chem., Int. Ed. 2002, 41: 3701

Google Scholar
10c Hilli F. White JM. Rizzacasa MA. Tetrahedron Lett. 2002, 43: 8507

Google Scholar
11a Bajwa N. Jennings MP. Tetrahedron Lett. 2008, 49: 390

Google Scholar
11b Furstner A. Kindler N. Tetrahedron Lett. 1996, 37: 7005

Google Scholar
11c Furstner A. Thiel OR. Kindler N. Bartkowska B. J. Org. Chem. 2000, 65: 7990

Google Scholar
11d Furstner A. Seidel G. Kindler N. Tetrahedron 1999, 55: 8215

Google Scholar
12 Holloway AG. Gel HHM. Rizzacasa AM. J. Org. Chem. 2003, 68: 2200

Crossref Google Scholar
13 Chakraborty TK. Chattopadhyay AK. J. Org. Chem. 2008, 73: 3578

Crossref Google Scholar
14a Stille JK. Groh BL. J. Am. Chem. Soc. 1987, 109: 813

Google Scholar
14b Farina V. Krishna B. J. Am. Chem. Soc. 1991, 113: 9585

Google Scholar
14c Mitchell TN. Synthesis 1992, 803

Google Scholar