Synthesis of exogonic acid and related compounds

Tomihiro Nishiyama; Joanne F. Woodhall; Elvie N. Lawson; William Kitching

doi:10.1021/jo00270a031

Synthesis of exogonic acid and related compounds

Tomihiro Nishiyama, Joanne F. Woodhall, Elvie N. Lawson, William Kitching^*

^*Corresponding author for this work

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

21 Citations (Scopus)

Abstract

Hydroxymercuration, cyclization, and reduction of appropriate hydroxy ketones or enones carrying a suitably located α,β-unsaturated ester function is an efficient route to exogonic acid (2-(carboxymethyl)-7-methyl-1,6-dioxaspiro[4.4]nonane), a resin constituent of the Brazilian tree Ipomoea operculata (Martin), and related [4.5] and [5.5] spiroketal systems. Procedures incorporating stereocontrol at C-2 and C-7 of exogonic acid are also reported and involve sequential alkylation with epoxypropane and l,2-epoxy-4-(tetrahydropyranyloxy)butane of anions (or dianions) derived from methyl acetoacetate or acetone dimethylhydrazone.

Original language	English
Pages (from-to)	2183-2189
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	54
Issue number	9
DOIs	https://doi.org/10.1021/jo00270a031
Publication status	Published - 28 Apr 1989
Externally published	Yes

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AU - Nishiyama, Tomihiro

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AU - Lawson, Elvie N.

AU - Kitching, William

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AB - Hydroxymercuration, cyclization, and reduction of appropriate hydroxy ketones or enones carrying a suitably located α,β-unsaturated ester function is an efficient route to exogonic acid (2-(carboxymethyl)-7-methyl-1,6-dioxaspiro[4.4]nonane), a resin constituent of the Brazilian tree Ipomoea operculata (Martin), and related [4.5] and [5.5] spiroketal systems. Procedures incorporating stereocontrol at C-2 and C-7 of exogonic acid are also reported and involve sequential alkylation with epoxypropane and l,2-epoxy-4-(tetrahydropyranyloxy)butane of anions (or dianions) derived from methyl acetoacetate or acetone dimethylhydrazone.

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Synthesis of exogonic acid and related compounds

Abstract

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