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Volumn 55, Issue 7, 2016, Pages 2498-2502

Tandem Allylboration-Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (-)-Clavosolide A

Author keywords

allylboration; lithiation borylation; natural products; Prins reaction; total synthesis

Indexed keywords

SYNTHESIS (CHEMICAL);

EID: 84954451112     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201511140     Document Type: Article
Times cited : (34)

References (75)
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    • The methodology is based on the Hoppe lithiation of carbamates
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    • For examples of the use of acrolein in Prins reactions see
    • For examples of the use of acrolein in Prins reactions see:
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    • Unfortunately, none of these reactions were successful with our methyl ether derivatives of xylose. Employing the previously described glycosidation conditions in the synthesis of (-)-clavosolide A (references [3f] and [3i]) with the methyl ether derivative of xylose a 1:1 mixture of diastereoisomers was obtained. Hong and Breit reported a 79:21 and a 77:23 ratio of anomers in a related glycosidation reaction (references [3j] and [3k], respectively)
    • A. Marra, J.-M. Mallet, C. Amatore, P. Sina, Synlett 1990, 572. Unfortunately, none of these reactions were successful with our methyl ether derivatives of xylose. Employing the previously described glycosidation conditions in the synthesis of (-)-clavosolide A (references [3f] and [3i]) with the methyl ether derivative of xylose a 1:1 mixture of diastereoisomers was obtained. Hong and Breit reported a 79:21 and a 77:23 ratio of anomers in a related glycosidation reaction (references [3j] and [3k], respectively).
    • (1990) Synlett , pp. 572
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    • Lithiation-deuteration experiments showed that this sequence was necessary, otherwise competing deprotonation of 3 a occurred at the allylic position
    • Lithiation-deuteration experiments showed that this sequence was necessary, otherwise competing deprotonation of 3 a occurred at the allylic position.
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    • For applications of late-stage lithiation-borylation methodologies in total synthesis see
    • For applications of late-stage lithiation-borylation methodologies in total synthesis see:
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    • This effect will of course be counterbalanced by its poorer ability to coordinate to the organolithium compared to the carbamate
    • This effect will of course be counterbalanced by its poorer ability to coordinate to the organolithium compared to the carbamate.
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    • Using TMEDA in place of the chiral ligand gave a 55:45 ratio of diastereomers showing that substrate control in the lithiation step was low. No lithiation occurred in the absence of diamines. For an intramolecular oxygen-directed lithiation of a carbamate by an acetonide see
    • Using TMEDA in place of the chiral ligand gave a 55:45 ratio of diastereomers showing that substrate control in the lithiation step was low. No lithiation occurred in the absence of diamines. For an intramolecular oxygen-directed lithiation of a carbamate by an acetonide see:, H. Helmke, D. Hoppe, Synlett 1995, 978.
    • (1995) Synlett , pp. 978
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.