Total synthesis of (.+-.)-granaticin

K Nomura, K Okazaki, K Hori…

Index: Nomura; Okazaki; Hori; Yoshii Journal of the American Chemical Society, 1987 , vol. 109, # 11 p. 3402 - 3408

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Citation Number: 34

Abstract

Abstract: A 20-step total synthesis of (f)-granaticin from tetralone 8 is described. Conversion of 8 to allylic alcohol 15 followed by a catalytic osmylation afforded triol 16 in a highly stereoselective manner, which was then cyclized to benzooxabicycle 18 through the agency of benzylic bromination with NBS. The intermediate 18 was efficiently converted to cyanophthalide 22, and its annulation with 5-tert-butoxy-2-furfurylideneacetone afforded ...