194934-55-9Relevant articles and documents
The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: The southern hemisphere EF segment
Paterson, Ian,Coster, Mark J.,Chen, David Y.-K.,Acena, Jose L.,Bach, Jordi,Keown, Linda E.,Trieselmann, Thomas
, p. 2420 - 2430 (2007/10/03)
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 Royal Society of Chemistry 2005.
Studies in marine macrolide synthesis: Stereocontrolled synthesis of the F-ring subunit of spongistatin 1 (Altohyrtin A).
Paterson, Ian,Keown, Linda E.
, p. 5727 - 5730 (2007/10/03)
The C36-C46 subunit 3, containing the F ring of spongistatin 1 (1), was prepared in 12 steps from ketone (R)-7. Key steps include: (i) the boron-mediated anti aldol reaction, 7 → 9; (ii) the Sharpless AD, 6 → 13; and (iii) an intramolecular hetero-Michael addition, followed by base-promoted equilibration to give 3.