A Direct Stereoselective Preparation of a Fish Pheromone and Application of the Zinc Porphyrin Tweezer Chiroptical Protocol in Its Stereochemical Assignment

作者：Ouedraogo Yannick P; Huang Longchuan; Torrente Mariana P; Proni Gloria; Chadwick Ekaterina; Wehmschulte Rudolf J; Nesnas Nasri^*

来源：Chirality, 2013, 25(9): 575-581.

DOI：10.1002/chir.22186

• goldfish pheromone
• stereoselective reduction
• cortexolone
• circular dichroism
• DFT
• computational modeling
• zinc porphyrin tweezer

A two-step stereoselective preparation of a goldfish pheromone, 17,20-dihydroxy-4-pregnen-3-one, is reported from the readily available cortexolone in 64% overall yield. The (20S)-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 17-hydroxyl and C18-methyl groups. Chirality 00:000-000:, 2013.

• 出版日期2013-9