Elsevier

Tetrahedron Letters

Volume 51, Issue 33, 18 August 2010, Pages 4320-4322
Tetrahedron Letters

A crotofolane-type diterpenoid and a rearranged nor-crotofolane-type diterpenoid with a new skeleton from the stems of Croton cascarilloides

https://doi.org/10.1016/j.tetlet.2010.06.033Get rights and content

Abstract

From the stems of Croton cascarilloides collected in the Okinawa Islands, a structurally rare crotofolane-type diterpenoid (1) and a rearranged nor-crotofalane, a new skeletal diterpenoid (2) were isolated. The structures were determined by X-ray crystallographic analyses, establishing their absolute stereostructures for the first time. Compound 2 was probably biosynthesized from 1 through several steps, such as decarboxylation, oxidation, C–C bond migration.

Section snippets

Supplementary data

Supplementary X-ray crystallographic data for 1 (CCDC 761004) and 2 (CCDC 761005) can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or [email protected]).

Acknowledgments

The authors are grateful for access to the superconducting NMR instrument at the Analytical Center of Molecular Medicine of the Hiroshima University Faculty of Medicine and an Applied Biosystem QSTAR XL system ESI (Nano Spray)-MS at the Analysis Center of Life Science of the Graduate School of Biomedical Sciences, Hiroshima University.

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