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  4. Synthesis of a C29-C51 Subunit of Spongistatin 1 (Altohyrtin A) Starting from (R)-3-Benzyloxy-2-methylpropan-1-ol
 
research article

Synthesis of a C29-C51 Subunit of Spongistatin 1 (Altohyrtin A) Starting from (R)-3-Benzyloxy-2-methylpropan-1-ol

Lemaire-Audoire, S.
•
Vogel, P.  
2000
The Journal of Organic Chemistry

A protected C29-C51 subunit ((+)-38) of Spongistatin 1 has been obtained. Key steps involve the aldol condensation of (3S,4R)-3-methyl-7-[(paramethoxybenzyl)oxy]-4-[(triethylsilyl)oxy]octan-2-one ((-)-6) with (tert-butyl)dimethylsilyl 4-deoxy-2,3-di-O-(methoxymethyl)-4-methyl-6-O-(tert-butyl)dimethylsilyl)--D-glycero-L-gluco-heptodialdo-1,5-pyranoside ((+)-7), and a C-glycosidation of (4R,7R&S,E)-7,8-dichloro-2-methylidene-1-(trimethylsilyl)oct-5-en-4-yl paramethoxybenzoate (16). Aldehyde (+)-7 was derived from (R)-3-benzyloxy-2-methylpropan-1-ol ((+)-10) in 13 formal steps but requiring the isolation of 5 intermediate products only. The longest linear synthetic scheme converts (+)-10 into (+)-38 in 2% overall yield (isolation of 11 intermediate products).

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Type
research article
DOI
10.1021/jo991642b
Author(s)
Lemaire-Audoire, S.
Vogel, P.  
Date Issued

2000

Published in
The Journal of Organic Chemistry
Volume

65

Issue

11

Start page

3346

End page

3356

Subjects

marine macrolide synthesis

•

sponge hyrtios-altum

•

catalytic asymmetric allylation

•

potent cytotoxic macrolides

•

enantioselective synthesis

•

cspongistatin-2

•

stereoselective synthesis

•

natural-products

•

stereocontrolled synthesis

•

absolute stereostructures

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LGSA  
Available on Infoscience
June 8, 2006
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/230379
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