SYNTHESIS OF THE NOVEL ANTILEUKEMIC TETRAHYDROCYCLOPENTA[B]BENZOFURAN, ROCAGLAMIDE AND RELATED SYNTHETIC STUDIES

A E  DAVEY; M J  SCHAEFFER; R J K  TAYLOR

SYNTHESIS OF THE NOVEL ANTILEUKEMIC TETRAHYDROCYCLOPENTA[B]BENZOFURAN, ROCAGLAMIDE AND RELATED SYNTHETIC STUDIES

A E DAVEY
, M J SCHAEFFER
, R J K TAYLOR

Chemistry

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

Abstract

Two approaches to the rocaglamide tricyclic skeleton are described. The first, which employs an unusual intramolecular dithianyl anion to carbonyl addition reaction, provides access to alpha-phenyl rocaglamide analogues. The second route involves an intramolecular keto aldehyde pinacolic coupling in the key step and can be used for the preparation of a whole range of rocaglamide analogues possessing both alpha- and beta-phenyl substituents. A total synthesis of rocaglamide, in racemic form, is described using this second approach. The synthetic route commences with phloroglucinol, an inexpensive and readily-available starting material, and takes only 8/9 steps giving an overall yield of >6%. The synthesis of 1 -epi-rocaglamide 29b is also described.

Original language	English
Pages (from-to)	2657-2666
Number of pages	10
Journal	Journal of the Chemical Society-Perkin Transactions 1
Issue number	20
Publication status	Published - 21 Oct 1992

Keywords

ORGANIC-SYNTHESIS
KETONES
CYCLIZATION
CONVERSION
REAGENTS
DIOLS

Cite this

@article{262f9d51fb9744a7afb8ebb9f1af518f,

title = "SYNTHESIS OF THE NOVEL ANTILEUKEMIC TETRAHYDROCYCLOPENTA[B]BENZOFURAN, ROCAGLAMIDE AND RELATED SYNTHETIC STUDIES",

abstract = "Two approaches to the rocaglamide tricyclic skeleton are described. The first, which employs an unusual intramolecular dithianyl anion to carbonyl addition reaction, provides access to alpha-phenyl rocaglamide analogues. The second route involves an intramolecular keto aldehyde pinacolic coupling in the key step and can be used for the preparation of a whole range of rocaglamide analogues possessing both alpha- and beta-phenyl substituents. A total synthesis of rocaglamide, in racemic form, is described using this second approach. The synthetic route commences with phloroglucinol, an inexpensive and readily-available starting material, and takes only 8/9 steps giving an overall yield of >6\%. The synthesis of 1 -epi-rocaglamide 29b is also described.",

keywords = "ORGANIC-SYNTHESIS, KETONES, CYCLIZATION, CONVERSION, REAGENTS, DIOLS",

author = "DAVEY, \{A E\} and SCHAEFFER, \{M J\} and TAYLOR, \{R J K\}",

year = "1992",

month = oct,

day = "21",

language = "English",

pages = "2657--2666",

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

issn = "0300-922X",

publisher = "The Royal Society of Chemistry",

number = "20",

}

TY - JOUR

T1 - SYNTHESIS OF THE NOVEL ANTILEUKEMIC TETRAHYDROCYCLOPENTA[B]BENZOFURAN, ROCAGLAMIDE AND RELATED SYNTHETIC STUDIES

AU - DAVEY, A E

AU - SCHAEFFER, M J

AU - TAYLOR, R J K

PY - 1992/10/21

Y1 - 1992/10/21

N2 - Two approaches to the rocaglamide tricyclic skeleton are described. The first, which employs an unusual intramolecular dithianyl anion to carbonyl addition reaction, provides access to alpha-phenyl rocaglamide analogues. The second route involves an intramolecular keto aldehyde pinacolic coupling in the key step and can be used for the preparation of a whole range of rocaglamide analogues possessing both alpha- and beta-phenyl substituents. A total synthesis of rocaglamide, in racemic form, is described using this second approach. The synthetic route commences with phloroglucinol, an inexpensive and readily-available starting material, and takes only 8/9 steps giving an overall yield of >6%. The synthesis of 1 -epi-rocaglamide 29b is also described.

AB - Two approaches to the rocaglamide tricyclic skeleton are described. The first, which employs an unusual intramolecular dithianyl anion to carbonyl addition reaction, provides access to alpha-phenyl rocaglamide analogues. The second route involves an intramolecular keto aldehyde pinacolic coupling in the key step and can be used for the preparation of a whole range of rocaglamide analogues possessing both alpha- and beta-phenyl substituents. A total synthesis of rocaglamide, in racemic form, is described using this second approach. The synthetic route commences with phloroglucinol, an inexpensive and readily-available starting material, and takes only 8/9 steps giving an overall yield of >6%. The synthesis of 1 -epi-rocaglamide 29b is also described.

KW - ORGANIC-SYNTHESIS

KW - KETONES

KW - CYCLIZATION

KW - CONVERSION

KW - REAGENTS

KW - DIOLS

M3 - Article

SN - 0300-922X

SP - 2657

EP - 2666

JO - Journal of the Chemical Society-Perkin Transactions 1

JF - Journal of the Chemical Society-Perkin Transactions 1

IS - 20

ER -