TY - GEN
T1 - Recent Advances for Synthesis of Scyphostatin and Utilization of Oxabicyclo[2.2.1]Heptene Toward Ethyl Shikimate
AU - Kuwata, Kazuaki
AU - Yamashita, Yasunobu
AU - Hanaya, Kengo
AU - Sugai, Takeshi
AU - Mizushima, Tohru
AU - Shoji, Mitsuru
N1 - Publisher Copyright:
© 2016 Elsevier B.V.
Copyright:
Copyright 2016 Elsevier B.V., All rights reserved.
PY - 2016
Y1 - 2016
N2 - Diels-Alder reaction of furan and acrylic chloride or acrylic acid provides oxabicyclo[2.2.1]heptenes with three chiral centers. We have prepared epoxycyclohexenol (+)-3 and acetate (-)-4 with high enantiomeric excess from Diels-Alder adduct 1 via lipase-mediated kinetic resolution. Recently, we synthesized scyphostatin hydrophilic core 52 and ethyl shikimate (10) via optically active alcohols 3 and 8, respectively. In this review, we are going to describe several syntheses of scyphostatin (6) and synthetic utility of polyoxygenated carbacycles such as 3, 4, 8, and 9 toward natural products.
AB - Diels-Alder reaction of furan and acrylic chloride or acrylic acid provides oxabicyclo[2.2.1]heptenes with three chiral centers. We have prepared epoxycyclohexenol (+)-3 and acetate (-)-4 with high enantiomeric excess from Diels-Alder adduct 1 via lipase-mediated kinetic resolution. Recently, we synthesized scyphostatin hydrophilic core 52 and ethyl shikimate (10) via optically active alcohols 3 and 8, respectively. In this review, we are going to describe several syntheses of scyphostatin (6) and synthetic utility of polyoxygenated carbacycles such as 3, 4, 8, and 9 toward natural products.
KW - diastereoselective reaction
KW - ethyl shikimate
KW - kinetic resolution
KW - oxabicycloheptene
KW - scyphostatin
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U2 - 10.1016/B978-0-444-63603-4.00012-7
DO - 10.1016/B978-0-444-63603-4.00012-7
M3 - Conference contribution
AN - SCOPUS:84976448938
SN - 9780444636034
T3 - Studies in Natural Products Chemistry
SP - 387
EP - 403
BT - Studies in Natural Products Chemistry, 2016
PB - Elsevier
ER -