Article

cis‐5‐Amino‐6‐hydroxycyclohexadiene as a Chiral Building Block: An Asymmetric Synthesis of (−)‐Swainsonine

Department of Chemistry, Stanford University, Stanford, CA 94305-5080 (USA), Fax: (+1) 650 725-0002
Chemistry (impact factor: 5.93). 10/1999; 5(11):3279 - 3284. DOI:10.1002/(SICI)1521-3765(19991105)5:11<3279::AID-CHEM3279>3.0.CO;2-4

ABSTRACT The four contiguous stereocenters of (−)-swainsonine were efficiently set in a 15-step synthesis with a 15 % overall yield and >99% ee. In order to differeniate the double bond in the key building block oxazolidin-2-one 2, a synthetic equivalent of oxazolidinone 3, is synthesized from the achiral diol 1 followed by a palladium-catalyzed desymmetrization of the meso-bis-carbamate.

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Keywords

15-step synthesis
 
achiral diol 1
 
double bond
 
key building block oxazolidin-2-one 2
 
oxazolidinone 3
 
synthetic equivalent
 

Barry M Trost