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Biosynthesis of the Verrucarins and Roridins. Part 4. The mode of incorporation of (3R)‐[(5R)‐5‐ 3 H]‐mevalonate into verrucarol. Evidence for the identity of the C(11)‐hydrogen atom of the trichothecane skeleton with the (5R)‐hydrogen atom of (3R)‐mevalonic acid
Author(s) -
Müller Beat,
Tamm Christoph
Publication year - 1975
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19750580217
Subject(s) - chemistry , stereochemistry , biosynthesis , identity (music) , hydrogen atom , mevalonate pathway , hydrogen , transformation (genetics) , biochemistry , enzyme , gene , organic chemistry , physics , alkyl , acoustics
Incorporation of (3R)‐[(5R)‐5‐ 3 H]‐mevalonate into verrucarin followed by hydrolyses to verrucarol (2) and transformation of the latter to the spirolactol 5 and the spirolactone 6 successively, demonstrate the identity of the C(11)‐hydrogen of the trichothecane skeleton with the 5‐‘pro‐R’ hydrogen atom of (3R)‐mevalonate.