TRANSITION-METAL MEDIATED SYNTHESIS OF (+/-)-CHUANGXINMYCIN METHYL-ESTER

M J  DICKENS; T J  MOWLEM; D A  WIDDOWSON; A M Z  SLAWIN; D J  WILLIAMS

TRANSITION-METAL MEDIATED SYNTHESIS OF (+/-)-CHUANGXINMYCIN METHYL-ESTER

M J DICKENS, T J MOWLEM, D A WIDDOWSON, A M Z SLAWIN, D J WILLIAMS

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

Abstract

Chromium mediated synthesis of 4-iodo-1-triisopropylsilylindole followed by 4-methoxycarbonylmethylthiation by palladium catalysed cross coupling with methoxycarbonylmethylthio(trialkyl)-stannane and aldol condensation gave the key alpha-thioacrylate intermediate 5. The Z-geometry of the major isomer of 5 was determined by X-ray crystal analysis. Closure of ring C by a novel fluoride ion catalysed formation of the 2a-3 bond completed a short synthesis of (+/-)-chuangxinmycin methyl ester 1 (R = Me).

Original language	English
Pages (from-to)	323-325
Number of pages	3
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	3
Publication status	Published - Feb 1992

Keywords

CHUANGXINMYCIN

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title = "TRANSITION-METAL MEDIATED SYNTHESIS OF (+/-)-CHUANGXINMYCIN METHYL-ESTER",

abstract = "Chromium mediated synthesis of 4-iodo-1-triisopropylsilylindole followed by 4-methoxycarbonylmethylthiation by palladium catalysed cross coupling with methoxycarbonylmethylthio(trialkyl)-stannane and aldol condensation gave the key alpha-thioacrylate intermediate 5. The Z-geometry of the major isomer of 5 was determined by X-ray crystal analysis. Closure of ring C by a novel fluoride ion catalysed formation of the 2a-3 bond completed a short synthesis of (+/-)-chuangxinmycin methyl ester 1 (R = Me).",

keywords = "CHUANGXINMYCIN",

author = "DICKENS, {M J} and MOWLEM, {T J} and WIDDOWSON, {D A} and SLAWIN, {A M Z} and WILLIAMS, {D J}",

year = "1992",

month = feb,

language = "English",

pages = "323--325",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "0300-922X",

publisher = "Chemical Society",

number = "3",

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TY - JOUR

T1 - TRANSITION-METAL MEDIATED SYNTHESIS OF (+/-)-CHUANGXINMYCIN METHYL-ESTER

AU - DICKENS, M J

AU - MOWLEM, T J

AU - WIDDOWSON, D A

AU - SLAWIN, A M Z

AU - WILLIAMS, D J

PY - 1992/2

Y1 - 1992/2

N2 - Chromium mediated synthesis of 4-iodo-1-triisopropylsilylindole followed by 4-methoxycarbonylmethylthiation by palladium catalysed cross coupling with methoxycarbonylmethylthio(trialkyl)-stannane and aldol condensation gave the key alpha-thioacrylate intermediate 5. The Z-geometry of the major isomer of 5 was determined by X-ray crystal analysis. Closure of ring C by a novel fluoride ion catalysed formation of the 2a-3 bond completed a short synthesis of (+/-)-chuangxinmycin methyl ester 1 (R = Me).

AB - Chromium mediated synthesis of 4-iodo-1-triisopropylsilylindole followed by 4-methoxycarbonylmethylthiation by palladium catalysed cross coupling with methoxycarbonylmethylthio(trialkyl)-stannane and aldol condensation gave the key alpha-thioacrylate intermediate 5. The Z-geometry of the major isomer of 5 was determined by X-ray crystal analysis. Closure of ring C by a novel fluoride ion catalysed formation of the 2a-3 bond completed a short synthesis of (+/-)-chuangxinmycin methyl ester 1 (R = Me).

KW - CHUANGXINMYCIN

M3 - Article

SN - 0300-922X

SP - 323

EP - 325

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 3

ER -

TRANSITION-METAL MEDIATED SYNTHESIS OF (+/-)-CHUANGXINMYCIN METHYL-ESTER

Abstract

Keywords

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