Synthesis 2016; 48(11): 1700-1710
DOI: 10.1055/s-0035-1561607
special topic
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Iterative Hydration of Polyene Strategy to Cryptocaryols A and B

Thomas J. Hunter
b  MilliporeSigma, 645 Science Drive, Madison, WI 53711, USA
,
Yanping Wang
a  Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA 02115, USA   Email: G.ODoherty@neu.edu
,
Jiamin Zheng
a  Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA 02115, USA   Email: G.ODoherty@neu.edu
,
George A. O’Doherty*
a  Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA 02115, USA   Email: G.ODoherty@neu.edu
› Author Affiliations
Further Information

Publication History

Received: 21 February 2016

Accepted after revision: 11 March 2016

Publication Date:
13 April 2016 (online)

Abstract

The development of two iterative asymmetric hydration approaches to the synthesis of all syn- and syn/anti/syn-1,3,5,7-tetraol motifs is described. These pseudo-symmetric products are synthetic precursors for 1,3-hexol products. The utility of the route to the all syn-1,3,5,7-tetraol diastereoisomer was demonstrated with its use in the synthesis of cryptocaryols A and B, as well as, stereoisomers.

Supporting Information

 
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