Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 15, Pages 3859-3862Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201400617
Keywords
furanocembranoids; macrocycles; metathesis; photoisomerization; total synthesis
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Funding
- Austrian FWF (Fonds zur Forderung der Wissenschaften) [M1322]
- Austrian Science Fund (FWF) [M1322] Funding Source: Austrian Science Fund (FWF)
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An asymmetric synthesis of the diterpenoid 17-deoxyprovidencin is described. Key steps include an aldol addition, a base-catalyzed Wipf-type furan formation, a Z-selective ring-closing metathesis for macrocyclization, a photochemical E/Z isomerization to a highly strained and conformationally restricted ring system, and the stereoselective formation of two epoxides on the ring.
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