THE TOTAL SYNTHESIS OF SWINHOLIDE-A .1. A STEREOCONTROLLED SYNTHESIS OF A C-19-C-32 SEGMENT

Authors
PATERSON I CUMMING JG WARD RA LAMBOLEY S
Citation
I. Paterson et al., THE TOTAL SYNTHESIS OF SWINHOLIDE-A .1. A STEREOCONTROLLED SYNTHESIS OF A C-19-C-32 SEGMENT, Tetrahedron, 51(34), 1995, pp. 9393-9412
Citations number
60
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
34
Year of publication
1995
Pages
9393 - 9412
Database
ISI
SICI code
0040-4020(1995)51:34<9393:TTSOS.>2.0.ZU;2-R
Abstract
The C-19-C-32 segment 10 of swinholide A was prepared in 15 steps (8% yield, 82% ds) from (+/-)-16. Key steps include (i) the Sharpless epox idation, 16 --> 17, (ii) the acetal allylation, 15 --> 23, (iii) the a nti aldol addition, 13 + 14 --> 12, and (iv) the alkene hydroboration, 30 --> 31.