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Total Synthesis of the Anticancer Marine Natural Product Mycalol
Author(s) -
Nageswara Rao K.,
Kumar Katragunta,
Ghosh Subhash
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701562
Subject(s) - total synthesis , chemistry , natural product , dihydroxylation , enantioselective synthesis , stereochemistry , diastereomer , sharpless asymmetric dihydroxylation , alkynylation , combinatorial chemistry , organic chemistry , catalysis
This communication describes a synthetic study of the originally proposed structure of mycalol ( 1 ) and the total synthesis of the actual structure of the anticancer marine natural product mycalol ( 2 ). The total synthesis of the originally proposed structure of mycalol ( 1 ) was targeted by a late‐stage asymmetric dihydroxylation, which resulted in an inseparable mixture of diastereomers. Thus a new strategy was developed for the total synthesis of the revised structure of mycalol ( 2 ); all the stereocentres except the C‐2′‐OH were created in an asymmetric fashion by using a Maruoka allylation, a Noyori asymmetric reduction, and an asymmetric alkynylation.