The preparation of 9-substituted Delta 5-octenolides: Synthesis of 8-deoxy-pseudo-ascidiatrienolide C

G A  McNaughtonSmith; R J K  Taylor

The preparation of 9-substituted Delta 5-octenolides: Synthesis of 8-deoxy-pseudo-ascidiatrienolide C

G A McNaughtonSmith, R J K Taylor

Chemistry

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

Abstract

Two routes have been explored for the preparation of the title 9 membered lactones. Lactonisation of a hydroxy acid bearing an embryonic unsaturated side chain followed by palladium-catalysed chain extension was shown to be problematic. The preferred procedure, which involved prior formation of the complete carbon skeleton followed by lactonisation using Mukaiyama conditions, was employed to prepare 8-deoxy-pseudo-Ascidiatrienolide C. The efficiency of the lactonisation process is particularly notable.

Original language	English
Pages (from-to)	2113-2124
Number of pages	12
Journal	Tetrahedron
Volume	52
Issue number	6
Publication status	Published - 5 Feb 1996

Keywords

HALICHONDRIA-OKADAI KADOTA
STEREOSELECTIVE SYNTHESIS
ORGANOMETALLIC REAGENTS
CLAISEN-REARRANGEMENT
PALLADIUM
LACTONES
ACID
LACTONIZATION
EFFICIENT
NEOHALICHOLACTONE

Cite this

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title = "The preparation of 9-substituted Delta 5-octenolides: Synthesis of 8-deoxy-pseudo-ascidiatrienolide C",

abstract = "Two routes have been explored for the preparation of the title 9 membered lactones. Lactonisation of a hydroxy acid bearing an embryonic unsaturated side chain followed by palladium-catalysed chain extension was shown to be problematic. The preferred procedure, which involved prior formation of the complete carbon skeleton followed by lactonisation using Mukaiyama conditions, was employed to prepare 8-deoxy-pseudo-Ascidiatrienolide C. The efficiency of the lactonisation process is particularly notable.",

keywords = "HALICHONDRIA-OKADAI KADOTA, STEREOSELECTIVE SYNTHESIS, ORGANOMETALLIC REAGENTS, CLAISEN-REARRANGEMENT, PALLADIUM, LACTONES, ACID, LACTONIZATION, EFFICIENT, NEOHALICHOLACTONE",

author = "McNaughtonSmith, {G A} and Taylor, {R J K}",

year = "1996",

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language = "English",

volume = "52",

pages = "2113--2124",

journal = "Tetrahedron",

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TY - JOUR

T1 - The preparation of 9-substituted Delta 5-octenolides: Synthesis of 8-deoxy-pseudo-ascidiatrienolide C

AU - McNaughtonSmith, G A

AU - Taylor, R J K

PY - 1996/2/5

Y1 - 1996/2/5

N2 - Two routes have been explored for the preparation of the title 9 membered lactones. Lactonisation of a hydroxy acid bearing an embryonic unsaturated side chain followed by palladium-catalysed chain extension was shown to be problematic. The preferred procedure, which involved prior formation of the complete carbon skeleton followed by lactonisation using Mukaiyama conditions, was employed to prepare 8-deoxy-pseudo-Ascidiatrienolide C. The efficiency of the lactonisation process is particularly notable.

AB - Two routes have been explored for the preparation of the title 9 membered lactones. Lactonisation of a hydroxy acid bearing an embryonic unsaturated side chain followed by palladium-catalysed chain extension was shown to be problematic. The preferred procedure, which involved prior formation of the complete carbon skeleton followed by lactonisation using Mukaiyama conditions, was employed to prepare 8-deoxy-pseudo-Ascidiatrienolide C. The efficiency of the lactonisation process is particularly notable.

KW - HALICHONDRIA-OKADAI KADOTA

KW - STEREOSELECTIVE SYNTHESIS

KW - ORGANOMETALLIC REAGENTS

KW - CLAISEN-REARRANGEMENT

KW - PALLADIUM

KW - LACTONES

KW - ACID

KW - LACTONIZATION

KW - EFFICIENT

KW - NEOHALICHOLACTONE

M3 - Article

SN - 0040-4020

VL - 52

SP - 2113

EP - 2124

JO - Tetrahedron

JF - Tetrahedron

IS - 6

ER -