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Synthesis of Elemane Bis‐Lactones from Santonin – Synthesis of the Reported Structure of seco ‐Isoerivanin Pseudo Acid and Formal Synthesis of (+)‐8‐Deoxyvernolepin
Author(s) -
Blay Gonzalo,
Cardona Luz,
García Begoña,
Lahoz Luisa,
Pedro José R.
Publication year - 2000
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 - 10.1002/1099-0690(200006)2000:11<2145::aid-ejoc2145>3.0.co;2-n
Subject(s) - chemistry , lactone , stereochemistry , epimer , total synthesis , electrophile , intramolecular force , yield (engineering) , chemical synthesis , intramolecular reaction , prins reaction , organic chemistry , catalysis , biochemistry , materials science , metallurgy , in vitro
The synthesis of the reported structure for seco ‐isoerivanin pseudo acid ( 1 ) and of an elemane bis‐lactone 5 from santonin ( 4 ) through a common vinylic precursor 12 is described. Compound 5 is a known intermediate in a previous synthesis of the antitumor compound (+)‐8‐deoxyvernolepin ( 3 ). The vinyl group of 12 underwent a regio‐ and diastereoselective anti addition of an external electrophile and an intramolecular condensation to yield either the selenolactone 13 or the hydroxylactone 17 . The lactones 13 and 17 served as key intermediates in the total synthesis of 1 and 5 respectively. A revision of the structure of seco ‐isoerivanin pseudo acid to the C‐10 epimer is suggested on the basis of comparison between the spectral data of the natural and synthetic products.