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Author(s): Akita H; Nakamura H; Ono M
Title: Total synthesis of (+)-macrosphelides A, C, E, F, and G based on enzymatic function
Source: CHIRALITY 15 (4): 352-359
Date: 2003 MAY 5
Document Type: Journal : Proceedings Paper
DOI:
Language: English
Comment:
Address: Toho Univ, Fac Pharmaceut Sci, Chiba 2748510, Japan.
Reprint: Akita, H, Toho Univ, Fac Pharmaceut Sci, 2-2-1 Miyama, Chiba 2748510,
Japan. E-mail:
Author Keywords: enzymatic resolution; lipase; total synthesis; macrolactonization;
antibiotics; macrosphelide
KeyWords Plus: CELL-CELL ADHESION; MACROSPHELIDE-C; CHEMOENZYMATIC SYNTHESES; KINETIC
RESOLUTION; SEA HARE; ESTERIFICATION; INHIBITORS; MACROLACTONIZATION;
EPOXIDATION; ROUTE
Abstract: The total synthesis of (+)-macrosphelide A (1) (18.5% overall yield in 11 steps), (+)-macrosphelide C (2) (25% overall yield in 9 steps), (+)- macrosphelide E (3) (23.9% overall yield in 11 steps), (+)- macrosphelide F (4) (20% overall yield in 9 steps), and (+)- macrosphelide G (5) (22% overall yield in 9 steps) was achieved from a chemoenzymatic reaction product (4R,5S)-4-benzyloxy-5-hydroxy-2 (E)- hexenoate 10.
Cited References: AKITA H, 1993, CHEM PHARM BULL, V41, P55 BODEN EP, 1985, J ORG CHEM, V50, P2394 DYONG I, 1976, ANGEW CHEM INT EDIT, V15, P302 EVANS DA, 1993, J ORG CHEM, V58, P2446 GAO Y, 1987, J AM CHEM SOC, V109, P5765 HAYASHI M, 1995, J ANTIBIOT, V48, P1435 ILLUMINATI G, 1981, ACCOUNTS CHEM RES, V14, P95 INANAGA J, 1979, B CHEM SOC JPN, V52, P1989 KOBAYASHI Y, 2000, TETRAHEDRON LETT, V41, P1559 KOBAYASHI Y, 2001, TETRAHEDRON LETT, V42, P2817 MARTIN VS, 1981, J AM CHEM SOC, V103, P6237 MITSUNOBU O, 1981, SYNTHESIS-STUTTGART, P1 NAKAMURA H, 2002, HETEROCYCLES, V57, P327 NAKAMURA H, 2002, TETRAHEDRON-ASYMMETR, V13, P705 NEISES B, 1978, ANGEW CHEM, V17, P522 NUMATA A, 1997, TETRAHEDRON LETT, V38, P8215 ONO M, 1996, TETRAHEDRON-ASYMMETR, V7, P2595 ONO M, 2000, TETRAHEDRON-ASYMMETR, V11, P2753 SAOTOME C, 2000, TETRAHEDRON-ASYMMETR, V11, P4137 SHARPLESS KB, 1992, J ORG CHEM, V57, P2768 SUNAZUKA T, 1997, J AM CHEM SOC, V119, P10247 TAKAMATSU S, 1997, J ANTIBIOT, V50, P878 YAMADA T, 2001, J CHEM SOC PERK T 1, P3046 |