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Merck

A concise total synthesis of amphidinolide T2.

Chemistry (Weinheim an der Bergstrasse, Germany) (2010-08-31)
Huoming Li, Jinlong Wu, Jialu Luo, Wei-Min Dai
PMID20803588
ABSTRACT

RCM + AD = T2: In the presence of the C16-methylene group, regioselective ring-closing metathesis (RCM) formed the (12E)-endocyclic double bond, which underwent Os-catalyzed asymmetric dihydroxylation (AD) to give the desired 12,13-diol intermediate required for the total synthesis of amphidinolide T2 in 16 linear steps in 8.0% overall yield.

MATERIALS
Product Number
Brand
Product Description
69822
Sigma-Aldrich
Methyl DL-lactate, ≥97.0% (GC)
230340
Sigma-Aldrich
(−)-Methyl L-lactate, 98%, optical purity ee: 97% (GLC)
277762
Sigma-Aldrich
(+)-Methyl D-lactate, 98%, optical purity ee: 96% (GLC)