A Novel Route to the Marasmane Skeleton via a Tandem Rearrangement−Cyclopropanation Reaction. Total Synthesis of (+)-Isovelleral

A general and efficient route to the marasmane skeleton is described. Total syntheses of two simple marasmanes (35 and 37) in racemic form were achieved using a MgI2-catalyzed rearrangement−cyclopropanation reaction of trimethylsilyl enol ether 31 derived from naphthalenone 30. The reaction proceeds...

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Bibliographic Details
Published in:Journal of organic chemistry 2001-04, Vol.66 (7), p.2350-2357
Main Authors: Bell, Roel P. L, Wijnberg, Joannes B. P. A, de Groot, Aede
Format: Article
Language:English
Subjects:
Basidiomycota - chemistry
Cyclopropanes - chemistry
EPS
Indenes - chemical synthesis
Laboratorium voor Organische chemie
Laboratory for Organic Chemistry
Mesylates - chemistry
Nuclear Magnetic Resonance, Biomolecular
Organic Chemistry
Organische Chemie
Sesquiterpenes - chemical synthesis
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Summary:A general and efficient route to the marasmane skeleton is described. Total syntheses of two simple marasmanes (35 and 37) in racemic form were achieved using a MgI2-catalyzed rearrangement−cyclopropanation reaction of trimethylsilyl enol ether 31 derived from naphthalenone 30. The reaction proceeds in high yield with complete diastereoselectivity and does not require the use of special cyclopropanation reagents. Application of this novel route to the marasmane framework was extended to the synthesis of naturally occurring (+)-isovelleral (41).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0015568