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Volumn 13, Issue 4, 2011, Pages 616-619

Total synthesis of broussonetine F: The orthoamide overman rearrangement of an allylic diol

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BROUSSONETINE F; PYRROLIDINE DERIVATIVE; TARTARIC ACID DERIVATIVE; TARTARIC ACID DIETHYL ESTER;

EID: 79951638435     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102856j     Document Type: Article
Times cited : (44)

References (38)
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    • 2690 We have also reported the formal total synthesis of (-)-morphine by the sequential Claisen rearrangement starting from d-glucal; see: Tetrahedron Lett. 2008, 49, 358-362
    • Hama, N.; Matsuda, T.; Sato, T.; Chida, N. Org. Lett. 2009, 11, 2687-2690 We have also reported the formal total synthesis of (-)-morphine by the sequential Claisen rearrangement starting from d-glucal; see: Tanimoto, H.; Saito, R.; Chida, N. Tetrahedron Lett. 2008, 49, 358-362
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    • We reported orthoamide-type Claisen rearrangements of allylic diols, which was successfully applied to the total synthesis of (-)-kainic acid; see:;
    • We reported orthoamide-type Claisen rearrangements of allylic diols, which was successfully applied to the total synthesis of (-)-kainic acid; see: Kitamoto, K.; Sampei, M.; Nakayama, Y.; Sato, T.; Chida, N. Org. Lett. 2010, 12, 5756-5759
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    • The sequential Overman rearrangement of bistrichloroimidate 18 provided bistrichloroacetamide i in 92% yield.
    • The sequential Overman rearrangement of bistrichloroimidate 18 provided bistrichloroacetamide i in 92% yield.
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    • Overman rearrangement of MOM-protected trichloroacetoimidate ii, which was synthesized from 16 in four steps, proceeded at lower temperature and much faster than the orthoamide version. As Danishefsky reported in ref 5b, we also observed that two diastereomers of orthoamide 19 underwent equilibration at room temperature.
    • Overman rearrangement of MOM-protected trichloroacetoimidate ii, which was synthesized from 16 in four steps, proceeded at lower temperature and much faster than the orthoamide version. As Danishefsky reported in ref 5b, we also observed that two diastereomers of orthoamide 19 underwent equilibration at room temperature.
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    • We believe that BHT might suppress the decomposition pathway via a radical species.
    • We believe that BHT might suppress the decomposition pathway via a radical species.
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    • Synthesis of vinyl iodide 12 is described in the Supporting Information.
    • Synthesis of vinyl iodide 12 is described in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.