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Volumn 60, Issue 52, 2004, Pages 12261-12267

Stereoselective synthesis of hyptolide and 6-epi-hyptolide

Author keywords

Asymmetric allylboration; Asymmetric ethynylation; Chiral pool; Hyptolide; Ring closing metathesis

Indexed keywords

LACTIC ACID DERIVATIVE; LACTONE DERIVATIVE;

EID: 9644272626     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.10.010     Document Type: Article
Times cited : (18)

References (46)
  • 33
  • 35
    • 9644305469 scopus 로고    scopus 로고
    • note
    • The use of two different silyl groups (e.g. TES and TBS) is not necessary in principle. However, we had initially planned the use of standard achiral ethynylating reagents (such as ethynylmagnesium bromide) in the reaction with 9. In anticipation of unsatisfactory diastereoselectivities in these reactions (as it turned out to be the case), we envisaged the oxidation of the resulting alcohols (10 +epimer) to a conjugated ynone, followed by stereoselective reduction. Since a free β-hydroxy carbonyl group might be convenient for that purpose, we placed an easily cleavable silyl group (TES) at this position. However, when we finally resorted to the asymmetric ethynylation of 9, we decided to maintain the already present TES group.
  • 36
    • 9644298564 scopus 로고    scopus 로고
    • note
    • 2S, the asymmetric ethynylation to 11 did not work.
  • 38
    • 0041780219 scopus 로고    scopus 로고
    • In addition to trimethylsilylacetylene, we also used 2-methyl-3-butyn-2- ol: D. Boyall, F. López, H. Sasaki, D. Frantz, and E.M. Carreira Org. Lett. 2 2000 4233 4236 However, whereas the addition step was successful, all attempts to cleave the acetone fragment solely led to decomposition
    • (2000) Org. Lett. , vol.2 , pp. 4233-4236
    • Boyall, D.1    López, F.2    Sasaki, H.3    Frantz, D.4    Carreira, E.M.5
  • 39
    • 0035969627 scopus 로고    scopus 로고
    • Aside from the contributions of Carreira's group, we have found only few examples of the use of their asymmetric ethynylation methodology: (a) R.K. Dieter, and H. Yu Org. Lett. 3 2001 3855 3858
    • (2001) Org. Lett. , vol.3 , pp. 3855-3858
    • Dieter, R.K.1    Yu, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.