Facile Total Synthesis of Carbonolides by Witting-Hoener Macro-Cyclization and Stereoselective Epoxidation

Noriyuki NAKAJIMA; Kouichi UOTO; Osamu YONEMITSU; Tadashi HATA

doi:10.1248/cpb.39.64

著者情報

キーワード: macrolide aglycon, carbonolide, total synthesis, Yamaguchi's esterification, Witting-Horner cyclization, stereoselective epoxidation, conformation, NOE

ジャーナルフリー

1991 年 39 巻 1 号 p. 64-74

DOI https://doi.org/10.1248/cpb.39.64

詳細

抄録

Sixteen-membered dienone type macrolide aglycons, carbonolide B (1), niddanolide (5), and platenolide W₁ (6), were synthesized highly stereoselectively from D-glucose via Yamaguchi's esterification of two fragments, 8 (C1-C10) and 9 (C11-C16), followed by Witting-Horner cyclization. Stereoselective epoxidation of the 16-membered dienones (34, 35) gave epoxy-enone-type macrolide aglycons, carbonolide A (2) and EOP aglycon (7).

責任著者(Corresponding author)

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