Total synthesis of the potent antitumor, bis-tetrahydrofuranyl annonaceous acetogenins (+)-asimicin and (+)-bullatacin

Thomas R. Hoye; Lushi Tan

doi:10.1016/0040-4039(95)00207-S

Total synthesis of the potent antitumor, bis-tetrahydrofuranyl annonaceous acetogenins (+)-asimicin and (+)-bullatacin

Thomas R. Hoye, Lushi Tan

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Abstract

Convergent syntheses of the title compounds involve: a bis-THF-subunit preparation via Sharpless' double asymmetric dihydroxylation and subsequent asymmetric epoxidation; preparation of the C(4)-hydroxybutenolide-containing subunit using a Stille butenolide synthesis; Pd^o-mediated coupling of these vinyl iodide and alkyne subunits; and selective Wilkinson reduction of the resulting enyne.

Original language	English (US)
Pages (from-to)	1981-1984
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	12
DOIs	https://doi.org/10.1016/0040-4039(95)00207-S
State	Published - Mar 20 1995

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title = "Total synthesis of the potent antitumor, bis-tetrahydrofuranyl annonaceous acetogenins (+)-asimicin and (+)-bullatacin",

abstract = "Convergent syntheses of the title compounds involve: a bis-THF-subunit preparation via Sharpless' double asymmetric dihydroxylation and subsequent asymmetric epoxidation; preparation of the C(4)-hydroxybutenolide-containing subunit using a Stille butenolide synthesis; Pdo-mediated coupling of these vinyl iodide and alkyne subunits; and selective Wilkinson reduction of the resulting enyne.",

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AU - Hoye, Thomas R.

AU - Tan, Lushi

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Y1 - 1995/3/20

N2 - Convergent syntheses of the title compounds involve: a bis-THF-subunit preparation via Sharpless' double asymmetric dihydroxylation and subsequent asymmetric epoxidation; preparation of the C(4)-hydroxybutenolide-containing subunit using a Stille butenolide synthesis; Pdo-mediated coupling of these vinyl iodide and alkyne subunits; and selective Wilkinson reduction of the resulting enyne.

AB - Convergent syntheses of the title compounds involve: a bis-THF-subunit preparation via Sharpless' double asymmetric dihydroxylation and subsequent asymmetric epoxidation; preparation of the C(4)-hydroxybutenolide-containing subunit using a Stille butenolide synthesis; Pdo-mediated coupling of these vinyl iodide and alkyne subunits; and selective Wilkinson reduction of the resulting enyne.

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U2 - 10.1016/0040-4039(95)00207-S

DO - 10.1016/0040-4039(95)00207-S

M3 - Article

AN - SCOPUS:0028912767

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 12

ER -

Total synthesis of the potent antitumor, bis-tetrahydrofuranyl annonaceous acetogenins (+)-asimicin and (+)-bullatacin

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