Stereocontrolled synthesis of ABC tricycle of solanoeclepin a

Masaatsu Adachi; Mai Torii; Toshio Nishikawa

doi:10.1055/s-0034-1380399

Stereocontrolled synthesis of ABC tricycle of solanoeclepin a

Masaatsu Adachi, Mai Torii, Toshio Nishikawa

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

7 Citations (Scopus)

Abstract

A tricyclic compound possessing oxabicyclo[2.2.1]heptane and seven-membered ring of solanoeclepin A, the most active hatching agent of potato cyst nematode, was synthesized from d-pantolactone. The synthesis features a tin-mediated 6-exo-trig radical cyclization followed by iodoetherification and ring-closing enyne metathesis.

Original language	English
Article number	658
Pages (from-to)	965-969
Number of pages	5
Journal	Synlett
Volume	26
Issue number	7
DOIs	https://doi.org/10.1055/s-0034-1380399
Publication status	Published - 2015 Apr 1
Externally published	Yes

Keywords

enyne metathesis
iodoetherification
natural products
radical cyclization
solanoeclepin A

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-0034-1380399

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abstract = "A tricyclic compound possessing oxabicyclo[2.2.1]heptane and seven-membered ring of solanoeclepin A, the most active hatching agent of potato cyst nematode, was synthesized from d-pantolactone. The synthesis features a tin-mediated 6-exo-trig radical cyclization followed by iodoetherification and ring-closing enyne metathesis.",

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AU - Torii, Mai

AU - Nishikawa, Toshio

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PY - 2015/4/1

Y1 - 2015/4/1

N2 - A tricyclic compound possessing oxabicyclo[2.2.1]heptane and seven-membered ring of solanoeclepin A, the most active hatching agent of potato cyst nematode, was synthesized from d-pantolactone. The synthesis features a tin-mediated 6-exo-trig radical cyclization followed by iodoetherification and ring-closing enyne metathesis.

AB - A tricyclic compound possessing oxabicyclo[2.2.1]heptane and seven-membered ring of solanoeclepin A, the most active hatching agent of potato cyst nematode, was synthesized from d-pantolactone. The synthesis features a tin-mediated 6-exo-trig radical cyclization followed by iodoetherification and ring-closing enyne metathesis.

KW - enyne metathesis

KW - iodoetherification

KW - natural products

KW - radical cyclization

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ER -

Stereocontrolled synthesis of ABC tricycle of solanoeclepin a

Abstract

Keywords

ASJC Scopus subject areas

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