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

doi:10.1002/1099-0690(200209)2002:18%3C3145::aid-ejoc3145%3E3.0.co;2-3

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
DOIs	https://doi.org/10.1002/1099-0690(200209)2002:18%3C3145::aid-ejoc3145%3E3.0.co;2-3
Publication status	Published - 2002

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ID number: ISI:000178079100008

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10.1002/1099-0690(200209)2002:18%3C3145::aid-ejoc3145%3E3.0.co;2-3

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Ruprah, P. K., Cros, J. P., Pease, J. E., Whittingham, W. G., & Williams, J. M. J. (2002). Studies towards the total synthesis of cycloaraneosene and ophiobolin M: A general strategy for the construction of the 5-8 bicyclic ring system. European Journal of Organic Chemistry, (18), 3145-3152. https://doi.org/10.1002/1099-0690(200209)2002:18%3C3145::aid-ejoc3145%3E3.0.co;2-3

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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.

UR - https://www.scopus.com/pages/publications/0036738714

U2 - 10.1002/1099-0690(200209)2002:18%3C3145::aid-ejoc3145%3E3.0.co;2-3

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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

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