Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids

Martin G. Banwell; Xinghua Ma; Rebecca M. Taylor; Anthony C. Willis

doi:10.1021/ol062020x

Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids

Martin G. Banwell^*, Xinghua Ma, Rebecca M. Taylor, Anthony C. Willis

^*Corresponding author for this work

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

30 Citations (Scopus)

Abstract

Reaction of N-methylindole (4) with 6,6-dibromobicyclo[3.1.0]hexane (5) in the presence of silver tetrafluoroborate affords conjugate 7 in 67% yield. This product can be readily elaborated to compounds 12b and 13b which embody the polycyclic frameworks associated with members of the hapalindole and fischerindole classes of alkaloids. The chiral-auxiliary-substituted 6,6-dibromobicyclo[3.1.0]hexanes 21 and 22 react with indole to give adducts likely to be useful in the enantioselective total synthesis of the title alkaloids.

Original language	English
Pages (from-to)	4959-4961
Number of pages	3
Journal	Organic Letters
Volume	8
Issue number	21
DOIs	https://doi.org/10.1021/ol062020x
Publication status	Published - 12 Oct 2006

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@article{a39bc43c28bb475e8147a65d7d1924ce,

title = "Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids",

abstract = "Reaction of N-methylindole (4) with 6,6-dibromobicyclo[3.1.0]hexane (5) in the presence of silver tetrafluoroborate affords conjugate 7 in 67\% yield. This product can be readily elaborated to compounds 12b and 13b which embody the polycyclic frameworks associated with members of the hapalindole and fischerindole classes of alkaloids. The chiral-auxiliary-substituted 6,6-dibromobicyclo[3.1.0]hexanes 21 and 22 react with indole to give adducts likely to be useful in the enantioselective total synthesis of the title alkaloids.",

author = "Banwell, \{Martin G.\} and Xinghua Ma and Taylor, \{Rebecca M.\} and Willis, \{Anthony C.\}",

year = "2006",

month = oct,

day = "12",

doi = "10.1021/ol062020x",

language = "English",

volume = "8",

pages = "4959--4961",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids

AU - Banwell, Martin G.

AU - Ma, Xinghua

AU - Taylor, Rebecca M.

AU - Willis, Anthony C.

PY - 2006/10/12

Y1 - 2006/10/12

N2 - Reaction of N-methylindole (4) with 6,6-dibromobicyclo[3.1.0]hexane (5) in the presence of silver tetrafluoroborate affords conjugate 7 in 67% yield. This product can be readily elaborated to compounds 12b and 13b which embody the polycyclic frameworks associated with members of the hapalindole and fischerindole classes of alkaloids. The chiral-auxiliary-substituted 6,6-dibromobicyclo[3.1.0]hexanes 21 and 22 react with indole to give adducts likely to be useful in the enantioselective total synthesis of the title alkaloids.

AB - Reaction of N-methylindole (4) with 6,6-dibromobicyclo[3.1.0]hexane (5) in the presence of silver tetrafluoroborate affords conjugate 7 in 67% yield. This product can be readily elaborated to compounds 12b and 13b which embody the polycyclic frameworks associated with members of the hapalindole and fischerindole classes of alkaloids. The chiral-auxiliary-substituted 6,6-dibromobicyclo[3.1.0]hexanes 21 and 22 react with indole to give adducts likely to be useful in the enantioselective total synthesis of the title alkaloids.

UR - https://www.scopus.com/pages/publications/33750309481

U2 - 10.1021/ol062020x

DO - 10.1021/ol062020x

M3 - Article

SN - 1523-7060

VL - 8

SP - 4959

EP - 4961

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Concise assembly of the polycyclic frameworks associated with the hapalindole and fischerindole alkaloids

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