The Stereocontrolled Total Synthesis of Altohyrtin A/Spongistatin 1: The Southern Hemisphere EF Segment
Author(s)
Paterson, I
Coster, MJ
Chen, DYK
Acena, JL
Bach, J
Keown, LE
Trieselmann, T
Griffith University Author(s)
Year published
2005
Metadata
Show full item recordAbstract
The fully functionalised C29-C51 southern hemisphere of altohyrtin A/spongistatin 1 (1), incorporating the E- and F-ring tetrahydropyran rings and the unsaturated side chain, has been synthesised in a highly convergent and stereocontrolled manner. Key steps in the synthesis of this phosphonium salt include four highly diastereoselective, substrate-controlled, boron aldol reactions to establish key C-C bonds and accompanying stereocentres, where the introduction of the chlorodiene side chain and the C47 hydroxyl-bearing centre were realised by exploiting remote stereoinduction from the F-ring tetrahydropyran.The fully functionalised C29-C51 southern hemisphere of altohyrtin A/spongistatin 1 (1), incorporating the E- and F-ring tetrahydropyran rings and the unsaturated side chain, has been synthesised in a highly convergent and stereocontrolled manner. Key steps in the synthesis of this phosphonium salt include four highly diastereoselective, substrate-controlled, boron aldol reactions to establish key C-C bonds and accompanying stereocentres, where the introduction of the chlorodiene side chain and the C47 hydroxyl-bearing centre were realised by exploiting remote stereoinduction from the F-ring tetrahydropyran.
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Journal Title
Organic & Biomolecular Chemistry
Volume
3
Subject
Medicinal and biomolecular chemistry
Organic chemistry