A tetrahydropentaleno[1,6a-a]naphthalen-4(2H)-one of defined relative stereochemistry for use towards Agariblazeispirol C

Alan R. Kennedy; William J. Kerr; Laura C. Paterson; Andrew Sutherland

doi:10.1107/S0108270110031781

A tetrahydropentaleno[1,6a-a]naphthalen-4(2H)-one of defined relative stereochemistry for use towards Agariblazeispirol C

Alan R. Kennedy, William J. Kerr, Laura C. Paterson, Andrew Sutherland

Pure And Applied Chemistry

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

1 Citation (Scopus)

Abstract

Towards the synthesis of the novel natural product Agariblazeispirol C, (5aR*,11bR*)-9-methoxy-3,8,11b-trimethyl-5,6,7,11b-tetrahydro-1H-pentaleno[1,6a-a]naphthalen-4(2H)-one, C20H24O2, has been prepared at a key stage of the preparative programme. The structure shows the desired stereochemical outcome of the central cyclization protocol, viz. a syn-relationship between the aliphatic methyl group on the 11b-position and the methylene group on the 5a-position [C-C-C-C = -34.57 (18)degrees].

Original language	English
Pages (from-to)	473-474
Number of pages	2
Journal	Acta Crystallographica Section C: Crystal Structure Communications
Volume	66
DOIs	https://doi.org/10.1107/S0108270110031781
Publication status	Published - Sep 2010

Keywords

alpha-carbonyl radicals
formal total-synthesis
beta-cedrene
cyclization
cedrone

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10.1107/S0108270110031781

Cite this

@article{74c9c4aea5104119ba3043776b57772f,

title = "A tetrahydropentaleno[1,6a-a]naphthalen-4(2H)-one of defined relative stereochemistry for use towards Agariblazeispirol C",

abstract = "Towards the synthesis of the novel natural product Agariblazeispirol C, (5aR*,11bR*)-9-methoxy-3,8,11b-trimethyl-5,6,7,11b-tetrahydro-1H-pentaleno[1,6a-a]naphthalen-4(2H)-one, C20H24O2, has been prepared at a key stage of the preparative programme. The structure shows the desired stereochemical outcome of the central cyclization protocol, viz. a syn-relationship between the aliphatic methyl group on the 11b-position and the methylene group on the 5a-position [C-C-C-C = -34.57 (18)degrees].",

keywords = "alpha-carbonyl radicals, formal total-synthesis, beta-cedrene, cyclization, cedrone",

author = "Kennedy, {Alan R.} and Kerr, {William J.} and Paterson, {Laura C.} and Andrew Sutherland",

year = "2010",

month = sep,

doi = "10.1107/S0108270110031781",

language = "English",

volume = "66",

pages = "473--474",

journal = "Acta Crystallographica Section C: Crystal Structure Communications",

issn = "0108-2701",

}

A tetrahydropentaleno[1,6a-a]naphthalen-4(2H)-one of defined relative stereochemistry for use towards Agariblazeispirol C. / Kennedy, Alan R.; Kerr, William J.; Paterson, Laura C.; Sutherland, Andrew.

In: Acta Crystallographica Section C: Crystal Structure Communications, Vol. 66, 09.2010, p. 473-474.

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

TY - JOUR

T1 - A tetrahydropentaleno[1,6a-a]naphthalen-4(2H)-one of defined relative stereochemistry for use towards Agariblazeispirol C

AU - Kennedy, Alan R.

AU - Kerr, William J.

AU - Paterson, Laura C.

AU - Sutherland, Andrew

PY - 2010/9

Y1 - 2010/9

N2 - Towards the synthesis of the novel natural product Agariblazeispirol C, (5aR*,11bR*)-9-methoxy-3,8,11b-trimethyl-5,6,7,11b-tetrahydro-1H-pentaleno[1,6a-a]naphthalen-4(2H)-one, C20H24O2, has been prepared at a key stage of the preparative programme. The structure shows the desired stereochemical outcome of the central cyclization protocol, viz. a syn-relationship between the aliphatic methyl group on the 11b-position and the methylene group on the 5a-position [C-C-C-C = -34.57 (18)degrees].

AB - Towards the synthesis of the novel natural product Agariblazeispirol C, (5aR*,11bR*)-9-methoxy-3,8,11b-trimethyl-5,6,7,11b-tetrahydro-1H-pentaleno[1,6a-a]naphthalen-4(2H)-one, C20H24O2, has been prepared at a key stage of the preparative programme. The structure shows the desired stereochemical outcome of the central cyclization protocol, viz. a syn-relationship between the aliphatic methyl group on the 11b-position and the methylene group on the 5a-position [C-C-C-C = -34.57 (18)degrees].

KW - alpha-carbonyl radicals

KW - formal total-synthesis

KW - beta-cedrene

KW - cyclization

KW - cedrone

UR - http://www.scopus.com/inward/record.url?scp=77956366834&partnerID=8YFLogxK

U2 - 10.1107/S0108270110031781

DO - 10.1107/S0108270110031781

M3 - Article

VL - 66

SP - 473

EP - 474

JO - Acta Crystallographica Section C: Crystal Structure Communications

JF - Acta Crystallographica Section C: Crystal Structure Communications

SN - 0108-2701

ER -

A tetrahydropentaleno[1,6a-a]naphthalen-4(2H)-one of defined relative stereochemistry for use towards Agariblazeispirol C

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Keywords

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Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

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A tetrahydropentaleno[1,6a-a]naphthalen-4(2H)-one of defined relative stereochemistry for use towards Agariblazeispirol C

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Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

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