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Stereoselective Synthesis and Absolute Configuration Determination of Xylariolide A
Author(s) -
Botubol José Manuel,
MacíasSánchez Antonio J.,
Collado Isidro G.,
HernándezGalán Rosario
Publication year - 2013
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.201201526
Subject(s) - chemistry , absolute configuration , dihydroxylation , diastereomer , epimer , stereoselectivity , stereochemistry , enantioselective synthesis , absolute (philosophy) , sharpless asymmetric dihydroxylation , organic chemistry , catalysis , philosophy , epistemology
The asymmetric synthesis of the antibacterial and antitumoral natural compound xylariolide A ( 1 ) and five stereoisomers has been achieved. The strategy is based on the one‐pot epoxidation/lactonisation or dihydroxylation/lactonisation of the hypothetical biosynthetic intermediate xylarioic A acid ( 8 ). The absolute configuration of xylariolide A was thus determined to be 3 R ,4 S ,5 R ,1′ R ,2′ R after the synthesis of 1 , two epimers, i.e., 1′‐ epi ‐xylariolide A ( 3 ) and 2′‐ epi ‐xylariolide A ( 4 ), and three more diastereoisomers 5 – 7 .
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