Toward the synthesis of spirastrellolide A: construction of two C1-C25 diastereomers containing the BC-spiroacetal

Ian Paterson; Edward A Anderson; Stephen M Dalby; Olivier Loiseleur

doi:10.1021/ol051405x

Toward the synthesis of spirastrellolide A: construction of two C1-C25 diastereomers containing the BC-spiroacetal

Org Lett. 2005 Sep 15;7(19):4125-8. doi: 10.1021/ol051405x.

Authors

Ian Paterson¹, Edward A Anderson, Stephen M Dalby, Olivier Loiseleur

Affiliation

¹ University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK. [email protected]

PMID: 16146368
DOI: 10.1021/ol051405x

Abstract

[reaction: see text] Stereo-controlled syntheses of two possible C1-C25 diastereomers of spirastrellolide A containing the cis-disubstituted tetrahydropyran and [6,6]-spiroacetal are reported, exploiting boron-mediated asymmetric aldol and allylation methodology.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetals / chemistry*
Carbon / chemistry*
Macrolides / chemical synthesis*
Macrolides / chemistry
Molecular Structure
Spiro Compounds
Stereoisomerism

Substances

Acetals
Macrolides
Spiro Compounds
spirastrellolide A
Carbon