37841-91-1Relevant articles and documents
A novel route to the marasmane skeleton via a tandem rearrangement-cyclopropanation reaction. Total synthesis of (+)-isovelleral
Bell,Wijnberg,De Groot
, p. 2350 - 2357 (2001)
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).
A Carbene Catalysis Strategy for the Synthesis of Protoilludane Natural Products
Hovey, M. Todd,Cohen, Daniel T.,Walden, Daniel M.,Cheong, Paul H.-Y.,Scheidt, Karl A.
, p. 9864 - 9867 (2017/08/08)
The Armillaria and Lactarius genera of fungi produce the antimicrobial and cytotoxic mellolide, protoilludane, and marasmane sesquiterpenoids. We report a unified synthetic strategy to access the protoilludane, mellolide, and marasmane families of natural products. The key features of these syntheses are 1) the organocatalytic, enantioselective construction of key chiral intermediates from a simple achiral precursor, 2) the utility of a key 1,2-cyclobutanediol intermediate to serve as a precursor to each natural product class, and 3) a direct chemical conversion of a protoilludane to a marasmane through serendipitous ring contraction, which provides experimental support for their proposed biosynthetic relationships.
A total synthesis of (+)-isovelleral. The absolute configuration of the russulaceae sesquiterpenes
Bergman,Hansson,Sterner,Wickberg
, p. 865 - 867 (2007/10/02)
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