X-ray crystallographic and NOE studies on the conformation of periplanones and their analogues

Masataka Mori, Kentaro Okada, Kazuko Shimazaki, Tatsuji Chuman, Shigefumi Kuwahara, Takeshi Kitahara, Kenji Mori

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The structure of periplanone-A was established by X-ray crystallographic analysis. In comparison of the X-ray and 1H NMR data with those of periplanone-B, it was shown that periphanone-A and -B adopt essentially the same conformation. The epoxy epimer of periplanone-A has 104-times lower biological activity than periplanone-A, and NMR analysis indicated that the molecule exists in a mixture of different conformera. The conformation of the regioisomer, in which the carbonyl and epoxy groups are transposed, was analysed by X-ray crystallography and 1H NMR spectroscopy. It is highly biologically active, and the conformation of the germacranoid skeleton was shown to be almost identical with that of periplanone-A. Simplified analogues and germacrene-D had relatively lower activity. NOE Experiments on these compounds suggested the conformational resemblance of their germacranoid skeletons with those of periplanone-A and -B.

Original languageEnglish
Pages (from-to)1769-1777
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number6
DOIs
Publication statusPublished - 1990 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'X-ray crystallographic and NOE studies on the conformation of periplanones and their analogues'. Together they form a unique fingerprint.

  • Cite this