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Asymmetric Total Synthesis of 16‐Methyleicos‐(4 E )‐en‐1‐yn‐3‐ol from the Marine Sponge Cribrochalina vasculum : Establishment of Absolute Configuration of Chiral Centers
Author(s) -
Gundoju Narayana Rao,
Bokam Ramesh,
Yalavarthi Nageswara Rao,
Shaik Karimulla,
Ponnapalli Mangala Gowri
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201803646
Subject(s) - absolute configuration , diastereomer , sponge , natural product , total synthesis , stereochemistry , chemistry , resolution (logic) , enantioselective synthesis , lipase , organic chemistry , catalysis , biology , enzyme , botany , computer science , artificial intelligence
The first total synthesis of 16‐Methyleicos‐(4 E )‐en‐1‐yn‐3‐ol, a bioactive component of the marine sponge Cribrochalina vasculum was achieved by Evans auxiliary methylation followed by resolution of the corresponding racemates using lipase formulation Novozyme 435 and Mosher's ester method. We report the asymmetric syntheses of four diastereomers ( 1 a‐d ) of the natural compound 1 and established the absolute configuration of chiral centers, leading to the revision of the natural product configuration from 3 S to 3 R .