An IMDA approach to tigliane and daphnane diterpenoids: Generation of rings A, B and C incorporating C-18

Philip C. Bulman Page; Colin M. Hayman; Heather L. McFarland; David J. Willock; Natasha M. Galea

doi:10.1055/s-2002-22700

An IMDA approach to tigliane and daphnane diterpenoids: Generation of rings A, B and C incorporating C-18

Philip C. Bulman Page, Colin M. Hayman, Heather L. McFarland, David J. Willock, Natasha M. Galea

Chemistry of Materials and Catalysis

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

21 Citations (Scopus)

Abstract

A synthesis of the tricyclic ring system of the daphnane and tigliane diterpenes, incorporating C-18 and the C-13 oxygen functionality found in phorbol and related compounds is described. The convergent synthesis utilizes an intramolecular Diels-Alder reaction as the key stereocontrolling step.

Original language	English
Pages (from-to)	583-587
Number of pages	5
Journal	Synlett
Issue number	4
DOIs	https://doi.org/10.1055/s-2002-22700
Publication status	Published - 2002

Keywords

AFFINITY
SYSTEMS
TUMOR PROMOTERS
daphnane
tigliane
FURANS IMDAF
SKELETON
phorbol
PHORBOL
MODEL
PROTEIN-KINASE-C
ENTRY
IMDA
synthesis
DIELS-ALDER REACTIONS

Access to Document

10.1055/s-2002-22700

Cite this

@article{cf7c7946e69b4b60859b06fae6cdf3b4,

title = "An IMDA approach to tigliane and daphnane diterpenoids: Generation of rings A, B and C incorporating C-18",

abstract = "A synthesis of the tricyclic ring system of the daphnane and tigliane diterpenes, incorporating C-18 and the C-13 oxygen functionality found in phorbol and related compounds is described. The convergent synthesis utilizes an intramolecular Diels-Alder reaction as the key stereocontrolling step.",

keywords = "AFFINITY, SYSTEMS, TUMOR PROMOTERS, daphnane, tigliane, FURANS IMDAF, SKELETON, phorbol, PHORBOL, MODEL, PROTEIN-KINASE-C, ENTRY, IMDA, synthesis, DIELS-ALDER REACTIONS",

author = "{Bulman Page}, {Philip C.} and Hayman, {Colin M.} and McFarland, {Heather L.} and Willock, {David J.} and Galea, {Natasha M.}",

year = "2002",

doi = "10.1055/s-2002-22700",

language = "English",

pages = "583--587",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "4",

}

TY - JOUR

T1 - An IMDA approach to tigliane and daphnane diterpenoids: Generation of rings A, B and C incorporating C-18

AU - Bulman Page, Philip C.

AU - Hayman, Colin M.

AU - McFarland, Heather L.

AU - Willock, David J.

AU - Galea, Natasha M.

PY - 2002

Y1 - 2002

N2 - A synthesis of the tricyclic ring system of the daphnane and tigliane diterpenes, incorporating C-18 and the C-13 oxygen functionality found in phorbol and related compounds is described. The convergent synthesis utilizes an intramolecular Diels-Alder reaction as the key stereocontrolling step.

AB - A synthesis of the tricyclic ring system of the daphnane and tigliane diterpenes, incorporating C-18 and the C-13 oxygen functionality found in phorbol and related compounds is described. The convergent synthesis utilizes an intramolecular Diels-Alder reaction as the key stereocontrolling step.

KW - AFFINITY

KW - SYSTEMS

KW - TUMOR PROMOTERS

KW - daphnane

KW - tigliane

KW - FURANS IMDAF

KW - SKELETON

KW - phorbol

KW - PHORBOL

KW - MODEL

KW - PROTEIN-KINASE-C

KW - ENTRY

KW - IMDA

KW - synthesis

KW - DIELS-ALDER REACTIONS

U2 - 10.1055/s-2002-22700

DO - 10.1055/s-2002-22700

M3 - Article

SN - 0936-5214

SP - 583

EP - 587

JO - Synlett

JF - Synlett

IS - 4

ER -