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Synthesis of Carotenoids in the Gliding Bacteria Taxeobacter : (all‐ E ,2′ R )‐3‐deoxy‐2′‐hydroxyflexixanthin
Author(s) -
Bireher Christof,
Pfander Hanspeter
Publication year - 1997
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.19970800317
Subject(s) - chemistry , stereochemistry , sharpless asymmetric dihydroxylation , carotenoid , enantioselective synthesis , bacteria , dihydroxylation , wittig reaction , organic chemistry , catalysis , food science , biology , genetics
The c 40 ‐carotenoid (all‐ E , 2′ R )‐deoxy‐2′‐hydroxyflexixanthin (=1′,2′‐dihydroxy‐3′,4′‐didehydro‐1′,2′‐dihydro‐β,ψ‐caroten‐4‐one;(2′ R )‐ 2 ) was synthesized according to a C 15 + C 10 + C 10 = C 40 strategy. The chiral centre was introduced into the C 10 ‐end group by the enantioselective Sharpless dihydroxylation. The four building blocks were coupled by applying four consecutive Witting reactions. By comparison of the CD spectra of the synthetic (2′ R )‐ 2 with those of 2 isolated from the gliding bacteria Taxeobacter , the configuration of natural 2 was determined as (2′ R ).