Toward the synthesis of spirastrellolide a: construction of a tetracyclic C26-C40 subunit containing the DEF-bis-spiroacetal

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

doi:10.1021/ol051403c

Toward the synthesis of spirastrellolide a: construction of a tetracyclic C26-C40 subunit containing the DEF-bis-spiroacetal

Org Lett. 2005 Sep 15;7(19):4121-4. doi: 10.1021/ol051403c.

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: 16146367
DOI: 10.1021/ol051403c

Abstract

[reaction: see text] A stereo-controlled synthesis of the fully elaborated C26-C40 tricyclic [5,6,6]-bis-spiroacetal of spirastrellolide A containing the C28 chlorine substituent is reported, exploiting asymmetric Sharpless dihydroxylation and boron-mediated allylation methodology.

Publication types

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

MeSH terms

Acetals / chemistry*
Macrolides / chemical synthesis*
Macrolides / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Polycyclic Compounds / chemistry*
Spiro Compounds / chemistry*

Substances

Acetals
Macrolides
Polycyclic Compounds
Spiro Compounds
spirastrellolide A