Practical total synthesis of fuligocandins A and B

Midori A. Arai; Junya Seto; Firoj Ahmed; Kento Uchiyama; Masami Ishibashi

doi:10.1055/s-0030-1258547

Practical total synthesis of fuligocandins A and B

Midori A. Arai, Junya Seto, Firoj Ahmed, Kento Uchiyama, Masami Ishibashi

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

Fuligocandins A and B, cycloanthranilylproline derivatives isolated from the myxomycete Fuligo candida, were synthesized efficiently by a Meyer-Schuster rearrangement, which gave Z-isomer with high selectivity. The absolute stereochemistry at C-11a of the natural products was determined to be S by comparison of the optical rotation of the natural products with synthetic counterparts derived from l-proline. This report is the first total synthesis of optically active fuligocandin B.

Original language	English
Pages (from-to)	2498-2502
Number of pages	5
Journal	Synlett
Issue number	16
DOIs	https://doi.org/10.1055/s-0030-1258547
Publication status	Published - 2010
Externally published	Yes

Keywords

Meyer-Schuster rearrangement
TRAIL
fuligocandin
myxomycete
total synthesis

ASJC Scopus subject areas

Organic Chemistry

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abstract = "Fuligocandins A and B, cycloanthranilylproline derivatives isolated from the myxomycete Fuligo candida, were synthesized efficiently by a Meyer-Schuster rearrangement, which gave Z-isomer with high selectivity. The absolute stereochemistry at C-11a of the natural products was determined to be S by comparison of the optical rotation of the natural products with synthetic counterparts derived from l-proline. This report is the first total synthesis of optically active fuligocandin B.",

keywords = "Meyer-Schuster rearrangement, TRAIL, fuligocandin, myxomycete, total synthesis",

author = "Arai, {Midori A.} and Junya Seto and Firoj Ahmed and Kento Uchiyama and Masami Ishibashi",

year = "2010",

doi = "10.1055/s-0030-1258547",

language = "English",

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T1 - Practical total synthesis of fuligocandins A and B

AU - Arai, Midori A.

AU - Seto, Junya

AU - Ahmed, Firoj

AU - Uchiyama, Kento

AU - Ishibashi, Masami

PY - 2010

Y1 - 2010

N2 - Fuligocandins A and B, cycloanthranilylproline derivatives isolated from the myxomycete Fuligo candida, were synthesized efficiently by a Meyer-Schuster rearrangement, which gave Z-isomer with high selectivity. The absolute stereochemistry at C-11a of the natural products was determined to be S by comparison of the optical rotation of the natural products with synthetic counterparts derived from l-proline. This report is the first total synthesis of optically active fuligocandin B.

AB - Fuligocandins A and B, cycloanthranilylproline derivatives isolated from the myxomycete Fuligo candida, were synthesized efficiently by a Meyer-Schuster rearrangement, which gave Z-isomer with high selectivity. The absolute stereochemistry at C-11a of the natural products was determined to be S by comparison of the optical rotation of the natural products with synthetic counterparts derived from l-proline. This report is the first total synthesis of optically active fuligocandin B.

KW - Meyer-Schuster rearrangement

KW - TRAIL

KW - fuligocandin

KW - myxomycete

KW - total synthesis

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SP - 2498

EP - 2502

JO - Synlett

JF - Synlett

IS - 16

ER -

Practical total synthesis of fuligocandins A and B

Abstract

Keywords

ASJC Scopus subject areas

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