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Volumn 70, Issue 24, 2005, Pages 9932-9939

De novo asymmetric synthesis of anamarine and its analogues

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; ISOMERS; REACTION KINETICS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 28044447643     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051681p     Document Type: Article
Times cited : (44)

References (36)
  • 14
    • 28044468455 scopus 로고    scopus 로고
    • note
    • Migual Carda and Alberto Marco noted that various stereoisomers of spicigerolide (2) have improved cytotoxicity against several cancer cell lines; see ref 5b.
  • 17
    • 0032580376 scopus 로고    scopus 로고
    • For a review on ring-closing metathesis reactions, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Chang, S.2
  • 19
    • 0035850265 scopus 로고    scopus 로고
    • For other uses of this pyranone formation in synthesis, see ref 3 and: (c) Pradaux, F.; Bouzbouz, S. Org. Lett. 2001, 3, 2233-2235.
    • (2001) Org. Lett. , vol.3 , pp. 2233-2235
    • Pradaux, F.1    Bouzbouz, S.2
  • 27
    • 0343072430 scopus 로고    scopus 로고
    • We initially considered the use of the catalytic asymmetric allylation reagent developed by Keck but were dissuaded by its use of stoichiometric tin. See: (a) Keck, G. E.; Krishnamurthy, D. Org. Synth. 1997, 75, 12.
    • (1997) Org. Synth. , vol.75 , pp. 12
    • Keck, G.E.1    Krishnamurthy, D.2
  • 30
    • 12344315246 scopus 로고    scopus 로고
    • In contrast to our results for acetonide 14 and its corresponding diol, Smith observed excellent regiocontrol (>10:1) in the dihydroxylation of related substituted epoxytrienoates. Similarly, they observed no significant loss of stereocontrol in the mismatched (slower) case. See: Smith, A. B., III; Walsh, S. P.; Frohn, M.; Duffey, M. O. Org. Lett. 2005, 7, 139-142.
    • (2005) Org. Lett. , vol.7 , pp. 139-142
    • Smith III, A.B.1    Walsh, S.P.2    Frohn, M.3    Duffey, M.O.4
  • 31
    • 28044459717 scopus 로고    scopus 로고
    • note
    • 2PHAL, see Scheme 3).
  • 32
    • 28044452042 scopus 로고    scopus 로고
    • note
    • The lack of E/Z selectivity (1:1) in the Wittig reaction with aldehyde 21 is quite surprising when compared to the nearly identical Wittig reaction with the C-5 diastereomeric aldehyde 13, where the E isomer 6b was formed with almost 10:1 selectivity. Although we cannot offer an explanation for this result, we did find this result to be reproducible.
  • 33
    • 28044459028 scopus 로고    scopus 로고
    • note
    • 2 reagent for this transformation; see ref 5a-d. We have found that the Leighton reagent works equally well in terms of stereochemical outcome and allows for a significantly simpler product isolation procedure; see ref 9.
  • 35
    • 28044473257 scopus 로고    scopus 로고
    • note
    • Experimental procedures for the synthesis of anamarine are presented in the Experimental Section. Complete experimental procedures and spectral data for all compounds are presented in the Supporting Information.
  • 36
    • 28044453141 scopus 로고    scopus 로고
    • note
    • These structures are not shown in the text.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.