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A Direct Stereoselective Preparation of a Fish Pheromone and Application of the Zinc Porphyrin Tweezer Chiroptical Protocol in Its Stereochemical Assignment
Author(s) -
Ouedraogo Yannick P.,
Huang Longchuan,
Torrente Mariana P.,
Proni Gloria,
Chadwick Ekaterina,
Wehmschulte Rudolf J.,
Nesnas Nasri
Publication year - 2013
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22186
Subject(s) - chemistry , stereoselectivity , porphyrin , yield (engineering) , chirality (physics) , zinc , epimer , stereochemistry , substrate (aquarium) , combinatorial chemistry , organic chemistry , catalysis , materials science , oceanography , geology , metallurgy , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
A two‐step stereoselective preparation of a goldfish pheromone, 17α,20β‐dihydroxy‐4‐pregnen‐3‐one, is reported from the readily available cortexolone in 64% overall yield. The (20 S )‐epimer was also synthesized in three steps from cortexolone with an overall yield of 47%. A microscale chiroptical technique based on a host/guest complexation mechanism between the substrate and a dimeric metalloporphyrin host (tweezer) was used to confirm the stereochemical assignment, while Density Functional Theory (DFT) calculations were employed to explain the high stereoselectivity induced by the 17α‐hydroxyl and C18‐methyl groups. Chirality 00:000–000:, 2013 . © 2013 Wiley Periodicals, Inc.