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

Philip Charles Bulman Page; Colin M. Hayman; Heather L.  McFarland; David J.  Willock; NM 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 Charles Bulman Page, Colin M. Hayman, Heather L. McFarland, David J. Willock, NM Galea

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

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
Article number	UNSP 1437-2096,E;2002,0,04,0583,0587,ftx,en;D00502ST.pd
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 - Apr 2002
Externally published	Yes

Keywords

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

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

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

year = "2002",

month = apr,

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

language = "English",

pages = "583--587",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag KG",

number = "4",

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TY - JOUR

T1 - An IMDA approach to tigliane and daphnane diterpenoids

T2 - Generation of rings A, B and C incorporating C-18

AU - Page, Philip Charles Bulman

AU - Hayman, Colin M.

AU - McFarland, Heather L.

AU - Willock, David J.

AU - Galea, NM

PY - 2002/4

Y1 - 2002/4

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 - phorbol

KW - synthesis

KW - tigliane

KW - daphnane

KW - IMDA

KW - PROTEIN-KINASE-C

KW - DIELS-ALDER REACTIONS

KW - TUMOR PROMOTERS

KW - FURANS IMDAF

KW - PHORBOL

KW - AFFINITY

KW - SKELETON

KW - SYSTEMS

KW - MODEL

KW - ENTRY

U2 - 10.1055/s-2002-22700

DO - 10.1055/s-2002-22700

M3 - Article

SP - 583

EP - 587

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 4

M1 - UNSP 1437-2096,E;2002,0,04,0583,0587,ftx,en;D00502ST.pd

ER -

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

Abstract

Keywords

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