Synthesis of the himandrine skeleton

Patrick D. O'Connor; Lewis N. Mander; Matthew M.W. McLachlan

doi:10.1021/ol036308n

Synthesis of the himandrine skeleton

Patrick D. O'Connor, Lewis N. Mander^*, Matthew M.W. McLachlan

^*Corresponding author for this work

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

34 Citations (Scopus)

Abstract

The hexacyclic himandrine skeleton 5, which is present in the most complex alkaloids of the tropical rain forest tree Galbulimima belgraveana, has been prepared for the first time. The synthesis begins from the known [3.2.1]benzobicyclooctene intermediate 10. Key steps include a Diels-Alder cycloaddition, Curtius rearrangement, Birch reduction, an intramolecular nucleophilic amination, and a palladium-mediated alkene amination.

Original language	English
Pages (from-to)	703-706
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	5
DOIs	https://doi.org/10.1021/ol036308n
Publication status	Published - 4 Mar 2004

Access to Document

10.1021/ol036308n

Cite this

@article{4d76e23d43be46a9811215d7236e75e8,

title = "Synthesis of the himandrine skeleton",

abstract = "The hexacyclic himandrine skeleton 5, which is present in the most complex alkaloids of the tropical rain forest tree Galbulimima belgraveana, has been prepared for the first time. The synthesis begins from the known [3.2.1]benzobicyclooctene intermediate 10. Key steps include a Diels-Alder cycloaddition, Curtius rearrangement, Birch reduction, an intramolecular nucleophilic amination, and a palladium-mediated alkene amination.",

author = "O'Connor, {Patrick D.} and Mander, {Lewis N.} and McLachlan, {Matthew M.W.}",

year = "2004",

month = mar,

day = "4",

doi = "10.1021/ol036308n",

language = "English",

volume = "6",

pages = "703--706",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - Synthesis of the himandrine skeleton

AU - O'Connor, Patrick D.

AU - Mander, Lewis N.

AU - McLachlan, Matthew M.W.

PY - 2004/3/4

Y1 - 2004/3/4

N2 - The hexacyclic himandrine skeleton 5, which is present in the most complex alkaloids of the tropical rain forest tree Galbulimima belgraveana, has been prepared for the first time. The synthesis begins from the known [3.2.1]benzobicyclooctene intermediate 10. Key steps include a Diels-Alder cycloaddition, Curtius rearrangement, Birch reduction, an intramolecular nucleophilic amination, and a palladium-mediated alkene amination.

AB - The hexacyclic himandrine skeleton 5, which is present in the most complex alkaloids of the tropical rain forest tree Galbulimima belgraveana, has been prepared for the first time. The synthesis begins from the known [3.2.1]benzobicyclooctene intermediate 10. Key steps include a Diels-Alder cycloaddition, Curtius rearrangement, Birch reduction, an intramolecular nucleophilic amination, and a palladium-mediated alkene amination.

UR - http://www.scopus.com/inward/record.url?scp=1642328227&partnerID=8YFLogxK

U2 - 10.1021/ol036308n

DO - 10.1021/ol036308n

M3 - Article

SN - 1523-7060

VL - 6

SP - 703

EP - 706

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Synthesis of the himandrine skeleton

Abstract

Access to Document

Other files and links

Fingerprint

Cite this