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https://hdl.handle.net/2440/100608
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Type: | Journal article |
Title: | Total synthesis and structure revision of (-)-siphonodictyal B and its biomimetic conversion into (+)-liphagal |
Author: | Markwell-Heys, A. Kuan, K. George, J. |
Citation: | Organic Letters, 2015; 17(17):4228-4231 |
Publisher: | American Chemical Society |
Issue Date: | 2015 |
ISSN: | 1523-7060 1523-7052 |
Statement of Responsibility: | Adrian W. Markwell-Heys, Kevin K. W. Kuan, and Jonathan H. George |
Abstract: | The structure of siphonodictyal B has been reassigned on the basis of the total synthesis of both possible C-8 epimers. The revised structure of siphonodictyal B was converted into liphagal by acid catalyzed rearrangement of a proposed epoxide intermediate. This biomimetic cascade features a succession of four distinct reactions (epoxidation, o-quinone methide formation, ring expansion, and benzofuran formation) that occur in a one-pot operation under mild conditions. During these studies we also isolated a surprisingly stable o-quinone methide that supports our mechanistic proposal for liphagal biosynthesis. |
Keywords: | Terpenes |
Description: | Published: August 21, 2015 |
Rights: | © 2015 American Chemical Society |
DOI: | 10.1021/acs.orglett.5b01973 |
Grant ID: | http://purl.org/au-research/grants/arc/DP130101827 http://purl.org/au-research/grants/arc/DE130100689 |
Published version: | http://dx.doi.org/10.1021/acs.orglett.5b01973 |
Appears in Collections: | Aurora harvest 7 Chemistry publications |
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