Synthese von optisch aktiven, natürlichen Carotioiden und strukturell verwandten Naturprodukten. X. Synthese von (3R, 3′ S, 5′ R)??Capsanthin,(3S, 5R, 3′ S, 5′ …

A Rüttimann, G Englert, H Mayer, GP Moss…

Index: Ruttimann; Engbert; Mayer; et al. Helvetica Chimica Acta, 1983 , vol. 66, # 7 p. 1939 - 1960

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Citation Number: 3

Abstract

Summary The synthesis of (3 R, 3'S, 5'R)-capsanthin (l),(3 S, 5 R, 3'S, 5'R)-capsorubin (2), and (3'S, 5'R)-cryptocapsin (3), found in the red paprika Capsicum annuum, is described using (+)-camphor (7) as a readily available starting material. As the key reaction, the unsaturated acetal 16 is hydroborated with (+)-diisopinocampheylborane to give the hydroxy ketone 12a in very high chemical and optical yield. A subsequent aldol condensation with ...