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Volumn 52, Issue 38, 2013, Pages 10052-10055

A synthesis of the chlorosulfolipid mytilipina a via a longest linear sequence of seven steps

Author keywords

kinetic resolution; lipids; metathesis; natural products; total synthesis

Indexed keywords

BROMOALLYLATION; CROSS METATHESIS; DIASTEREOSELECTIVE; KINETIC RESOLUTION; LINEAR SEQUENCE; METATHESIS; NATURAL PRODUCTS; TOTAL SYNTHESIS;

EID: 84884278517     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201304565     Document Type: Article
Times cited : (50)

References (39)
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    • Angew. Chem. Int. Ed. 2011, 50, 7940-7943.
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 7940-7943
  • 26
    • 33644959351 scopus 로고    scopus 로고
    • The addition of organometallic nucleophiles to α-chloroaldehydes generally proceeds to afford the anti product, consistent with the polar Felkin-Anh model (hyperconjugative stabilization of the transition state/steric control), though the Cornforth model (dipole minimization/steric control) also accounts for the stereochemistry of the products. For an excellent discussion and lead reference, see:, V. J. Cee, C. J. Cramer, D. A. Evans, J. Am. Chem. Soc. 2006, 128, 2920-2930.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 2920-2930
    • Cee, V.J.1    Cramer, C.J.2    Evans, D.A.3
  • 27
    • 84872539157 scopus 로고    scopus 로고
    • Carbonyl additions to simple α-chloroaldehydes are often highly diastereoselective. See:, R. Britton, B. Kang, Nat. Prod. Rep. 2013, 30, 227-236.
    • (2013) Nat. Prod. Rep. , vol.30 , pp. 227-236
    • Britton, R.1    Kang, B.2
  • 35
    • 79957751484 scopus 로고    scopus 로고
    • For the most advanced system to date for catalytic asymmetric dichlorination of allylic alcohols, and an excellent lead reference, see:, K. C. Nicolaou, N. L. Simmons, Y. Ying, P. M. Heretsch, J. S. Chen, J. Am. Chem. Soc. 2011, 133, 8134-8137. For a stoichiometric reagent system that enabled enantioselective dichlorination in the context of a complex natural product synthesis, see
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 8134-8137
    • Nicolaou, K.C.1    Simmons, N.L.2    Ying, Y.3    Heretsch, P.M.4    Chen, J.S.5
  • 39
    • 84884256569 scopus 로고    scopus 로고
    • R. W. Geisser, D. Sc. Dissertation, ETH Zürich, 2010
    • The Carreira group used a Sharpless epoxidation of racemic anti-4,5-dichloro-2-buten-1-ol followed by diastereomer separation to render their synthesis of mytilipin A enantioselective: R. W. Geisser, D. Sc. Dissertation, ETH Zürich, 2010.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.