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Asymmetric catalysis route to anti,anti stereotriads, illustrated by applications.

Organic letters (2008-03-05)
Kathlyn A Parker, Qiuzhe Xie
ABSTRACT

A short sequence based on asymmetric catalysis, chirality transfer, and an optimized carbometallation protocol gave an anti,anti stereotriad building block in six steps. Both enantiomers of the chirality source, N-methyl ephedrine, are inexpensive, and the auxiliary is recoverable. In one chiral series, the building block was converted to the "B-2" intermediate in Miyashita's synthesis of scytophycin C; in the enantiomeric series, it was converted to a key intermediate for aplyronine A and to the polyketide "cap" for the callipeltins.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(1R,2S)-(-)-N-甲基麻黄碱, 99%
Supelco
甲基麻黄碱标准液 溶液, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant®