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Solution‐ and Soluble‐Polymer Supported Asymmetric Syntheses of Six‐Membered Ring Prostanoids
Author(s) -
LópezPelegrín José A.,
Janda Kim D.
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20000602)6:11<1917::aid-chem1917>3.0.co;2-7
Subject(s) - chemistry , ring (chemistry) , conjugate , trifluoromethanesulfonate , alkylation , stereochemistry , enone , combinatorial chemistry , molecule , organic chemistry , catalysis , mathematical analysis , mathematics
An asymmetric synthesis of prostanoids containing a six‐membered ring core structure (11a‐homoprostaglandins), both in solution and using non‐cross‐linked polystyrene (NCPS) as a soluble support, was developed. Target molecule 1 was generated in a convergent fashion using a three‐component coupling strategy, wherein chiral enone ( R )‐ 2 was the precursor of the central ring and the cuprate 3 and triflate 4 were used to introduce the side chains. The chiral center of ( R )‐ 2 directed the facial selectivity of the conjugate addition reaction which then dictated the stereochemical outcome of the subsequent α alkylation. Attachment of a six‐membered ring scaffold to NCPS facilitated purification without compromising synthetic yields, still allowed 1 H‐NMR analysis of the intermediates in the synthesis, and provided an avenue for the construction of six‐membered ring prostanoid libraries.