Studies towards the total synthesis of cycloaraneosene and ophiobolin M: A general strategy for the construction of the 5-8 bicyclic ring system

P K Ruprah; J P Cros; J E Pease; W G Whittingham; J M J Williams

Studies towards the total synthesis of cycloaraneosene and ophiobolin M: A general strategy for the construction of the 5-8 bicyclic ring system

P K Ruprah, J P Cros, J E Pease, W G Whittingham, J M J Williams

Department of Chemistry

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Abstract

The synthesis of the core unit of cycloaraneosene and ophiobolin M has been investigated, following a general strategy applicable to both 5-8 bicyclic systems. The synthetic strategy includes a ring-closing metathesis reaction to generate the central eight-membered ring as well as a palladium-mediated coupling of a Grignard reagent to introduce the exocyclic side-chain. The stereochemistry of the ring junction is also discussed and moderate diastereoselectivity has been achieved. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Original language	English
Pages (from-to)	3145-3152
Number of pages	8
Journal	European Journal of Organic Chemistry
Issue number	18
Publication status	Published - 2002

Bibliographical note

ID number: ISI:000178079100008

Cite this

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abstract = "The synthesis of the core unit of cycloaraneosene and ophiobolin M has been investigated, following a general strategy applicable to both 5-8 bicyclic systems. The synthetic strategy includes a ring-closing metathesis reaction to generate the central eight-membered ring as well as a palladium-mediated coupling of a Grignard reagent to introduce the exocyclic side-chain. The stereochemistry of the ring junction is also discussed and moderate diastereoselectivity has been achieved. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.",

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year = "2002",

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pages = "3145--3152",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

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T1 - Studies towards the total synthesis of cycloaraneosene and ophiobolin M: A general strategy for the construction of the 5-8 bicyclic ring system

AU - Ruprah, P K

AU - Cros, J P

AU - Pease, J E

AU - Whittingham, W G

AU - Williams, J M J

N1 - ID number: ISI:000178079100008

PY - 2002

Y1 - 2002

N2 - The synthesis of the core unit of cycloaraneosene and ophiobolin M has been investigated, following a general strategy applicable to both 5-8 bicyclic systems. The synthetic strategy includes a ring-closing metathesis reaction to generate the central eight-membered ring as well as a palladium-mediated coupling of a Grignard reagent to introduce the exocyclic side-chain. The stereochemistry of the ring junction is also discussed and moderate diastereoselectivity has been achieved. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

AB - The synthesis of the core unit of cycloaraneosene and ophiobolin M has been investigated, following a general strategy applicable to both 5-8 bicyclic systems. The synthetic strategy includes a ring-closing metathesis reaction to generate the central eight-membered ring as well as a palladium-mediated coupling of a Grignard reagent to introduce the exocyclic side-chain. The stereochemistry of the ring junction is also discussed and moderate diastereoselectivity has been achieved. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

M3 - Article

SN - 1434-193X

SP - 3145

EP - 3152

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 18

ER -

Studies towards the total synthesis of cycloaraneosene and ophiobolin M: A general strategy for the construction of the 5-8 bicyclic ring system

Abstract

Bibliographical note

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