Tetrahedron Letters p. 9321 - 9324 (1996)
Update date:2022-08-04
Topics:
Masaki, Yukio
Yoshizawa, Kazuhiro
Itoh, Akichika
Optically active natural thromboxane B2 (TXB2) was synthesized from (R,R)-tartaric acid as only chiral source. The synthesis was achieved through regio- and stereoselective introduction of acetate moiety at the C2-position of the 6,8-dioxabicyclo[3.2.1]octene derivative (2) to provide an acetamide derivative (6), partial ring opening of 6 to give a pyranoid (10), and construction of the C15-hydroxyl group of TXB2 by stereospecific allylic transposition of the inherent chirality of tartaric acid in the transallylic acetate (18).
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