Issue 74, 2013
From the journal:

Chemical Communications

First total synthesis of (−)-sinularianin B†

Koichiro Otaa  and  Hiroaki Miyaoka*a  

* Corresponding authors

a School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
E-mail: miyaokah@toyaku.ac.jp
Fax: +81-42-676-3073
Tel: +81-42-676-3080

Abstract

The first enantioselective total synthesis of (−)-sinularianin B, a structurally unique sesquiterpenoid isolated from the Formosan soft coral Sinularia sp., has been accomplished in 16 steps with 39.5% overall yield. Key transformations include formation of a cyclopentane possessing a tertiary hydroxy group via a tandem intermolecular–intramolecular alkylation involving a 5-endo cyclization.

Graphical abstract: First total synthesis of (−)-sinularianin B

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Article information

DOI
https://doi.org/10.1039/C3CC44303E
Article type
Communication
Submitted
07 Jun 2013
Accepted
02 Jul 2013
First published
02 Jul 2013

Chem. Commun., 2013,49, 8148-8150

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First total synthesis of (−)-sinularianin B

K. Ota and H. Miyaoka, Chem. Commun., 2013, 49, 8148 DOI: 10.1039/C3CC44303E

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