A concise total synthesis of amphidinolide T2.

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)

277762

Sigma-Aldrich

(+)-Methyl D-lactate, 98%, optical purity ee: 96% (GLC)

230340

Sigma-Aldrich

(−)-Methyl L-lactate, 98%, optical purity ee: 97% (GLC)