An expedient synthesis of spiroketals: model studies for the calylucin C16-C25 fragment

Ari Koskinen; Vesa Rauhala; Marta Nevalainen

An expedient synthesis of spiroketals: model studies for the calylucin C16-C25 fragment

Ari Koskinen, Vesa Rauhala, Marta Nevalainen

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

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Abstract

Anew short strategy to prepare the spiroketal fragment of calyculins is presented. A novel Seyferth–Gilbert type homologation of hindered lactols to the corresponding alkynes has been achieved for the first time. The spirocyclization was achieved efficiently via a DIHMA (double intramolecular hetero-Michael addition) process of this hindered ynone. The spirocyclization rate is not dependent on the stereochemistry of the alkoxy substituent in the oxolane ring.

Original language	English
Pages (from-to)	9199-9204
Journal	Tetrahedron
Issue number	60
Publication status	Published - 2004
MoE publication type	A1 Journal article-refereed

Keywords

enantioselectivity
natural products
spiroketals

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An_expedient_synthesis_of_spiroketals_Model_studieAccepted author manuscript, 289 KBLicence: CC BY-NC-ND

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title = "An expedient synthesis of spiroketals: model studies for the calylucin C16-C25 fragment",

abstract = "Anew short strategy to prepare the spiroketal fragment of calyculins is presented. A novel Seyferth–Gilbert type homologation of hindered lactols to the corresponding alkynes has been achieved for the first time. The spirocyclization was achieved efficiently via a DIHMA (double intramolecular hetero-Michael addition) process of this hindered ynone. The spirocyclization rate is not dependent on the stereochemistry of the alkoxy substituent in the oxolane ring.",

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journal = "Tetrahedron",

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T1 - An expedient synthesis of spiroketals: model studies for the calylucin C16-C25 fragment

AU - Koskinen, Ari

AU - Rauhala, Vesa

AU - Nevalainen, Marta

PY - 2004

Y1 - 2004

N2 - Anew short strategy to prepare the spiroketal fragment of calyculins is presented. A novel Seyferth–Gilbert type homologation of hindered lactols to the corresponding alkynes has been achieved for the first time. The spirocyclization was achieved efficiently via a DIHMA (double intramolecular hetero-Michael addition) process of this hindered ynone. The spirocyclization rate is not dependent on the stereochemistry of the alkoxy substituent in the oxolane ring.

AB - Anew short strategy to prepare the spiroketal fragment of calyculins is presented. A novel Seyferth–Gilbert type homologation of hindered lactols to the corresponding alkynes has been achieved for the first time. The spirocyclization was achieved efficiently via a DIHMA (double intramolecular hetero-Michael addition) process of this hindered ynone. The spirocyclization rate is not dependent on the stereochemistry of the alkoxy substituent in the oxolane ring.

KW - enantioselectivity

KW - natural products

KW - spiroketals

KW - enantioselectivity

KW - natural products

KW - spiroketals

KW - enantioselectivity

KW - natural products

KW - spiroketals

M3 - Article

SP - 9199

EP - 9204

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 60

ER -