Water overcomes methyl group directing effects in epoxide-opening cascades

Journal of the American Chemical Society

Volumn 131, Issue 19, 2009, Pages 6678-6679

  Morten, Christopher J ^a   Jamison, Timothy F ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS;

CHEMICAL EQUATIONS; METHYL GROUP; TEMPLATED; TETRAHYDROPYRAN;

HYDROCARBONS;

BREVETOXIN; EPOXIDE; METHYL GROUP; WATER; BIOLOGICAL PRODUCT; BREVETOXIN B; MARINE TOXIN; METHANE; OXOCIN DERIVATIVE;

ARTICLE; BIOSYNTHESIS; CHEMICAL REACTION; CYCLIZATION; CHEMISTRY; SYNTHESIS;

BIOLOGICAL PRODUCTS; CYCLIZATION; EPOXY COMPOUNDS; MARINE TOXINS; METHANE; OXOCINS; WATER;

EID: 67650301679     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9025243     Document Type: Article

References (15)

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9. Distal and proximal Me groups are shown in red and blue, respectively.
10. In cascades to form polyoxepanes, trans-disubstituted epoxides can be accommodated to some extent, generally with lower yields (see refs 3c and 3d).
11. Endo-selective cyclization with methoxymethyl substitution on the epoxide proximal to the pendent nucleophile was reported by Murai and coworkers. See: (a) Fujiwara, K.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1995, 36, 8063.
12. (b) Fujiwara, K.; Mishima, H.; Amano, A.; Tokiwano, T.; Murai, A. Tetrahedron Lett. 1998, 39, 393.
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15. A 6,5-fused side product arising from exo opening was also collected in 39% yield (see the Supporting Information).