Synthesis of maremycins A and D1 via cycloaddition of a nitrone with (E)-3-ethylidene-1-methylindolin-2-one

Organic Letters

Volumn 10, Issue 10, 2008, Pages 2043-2046

  Ueda, Tohru ^a   Inada, Mitsuhide ^a   Okamoto, Iwao ^a   Morita, Nobuyoshi ^a   Tamura, Osamu ^a  

^a SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

(E) 3 ETHYLIDENE 1 METHYLINDOLIN 2 ONE; (E)-3-ETHYLIDENE-1-METHYLINDOLIN-2-ONE; INDOLE DERIVATIVE; MAREMYCIN A; MAREMYCIN D1; NITROGEN OXIDE; NITRONES;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CYCLIZATION; INDOLES; MOLECULAR STRUCTURE; NITROGEN OXIDES; STEREOISOMERISM;

EID: 47049111461     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800515w     Document Type: Article

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29. Nitrone 10 and 3-ethylidene-1-methylindolin-2-one (9) are highly polar compounds whose oxygen atom may possess donating character, and hence they would not undergo stabilization in hexane, which has low polarity and low accepting ability. Since cycloreversion from cycloadducts 12 and 13 leading to nitrone 10 and indolinone 9 would become unfavorable in hexane, dominance of cycloadduct 13 may be suppressed, affording a 1:1 mixture of 12 and 13.
30. Computation (6-31G*) indicated that cycloadduct 13 is more stable by 1.47 kcal/mol than cycloadduct 12 (Supporting Information).