STEREOCONTROLLED SYNTHESYS OF 22-HYDROXY-23-ACETYLENIC STEROIDS, KEY INTERMEDIATES IN STEROID SIDE CHAIN CONSTRUCTION. OBSERVATION OF A DIRECTIVE EFFECT BY AN α-CHIRAL SITE DURING ASYMMETRIC REDUCTION WITH B-3-PINANYL-9-BBN (ALPINE-BORANE)

DOI: 10.1016/S0040-4039(01)81738-X

Source and publish data:

Tetrahedron Letters p. 5981 - 5984 (1984)

Update date:2022-08-05

Topics:

Authors:

Midland, M. Mark

Kwon, Young C.

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Article abstract of DOI:10.1016/S0040-4039(01)81738-X

An efficient stereoselective synthesis of 22-R- and 22-S-hydroxy-23-acetylenic steroids has been developed using R-Alpine-Borane (125:1, R:S) and L-Selectride (1:11, R:S) to reduce the 22-keto-steroid.S-Alpine-Borane provides an unexpectedly low 1:2.7, R:S ratio due to the influence of the α-chiral center at C-20 of the steroid.

Full text of DOI:10.1016/S0040-4039(01)81738-X

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