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Volumn , Issue 2, 2005, Pages 294-298

γ-allenyl allyl benzothiazole sulfonyl anions undergo cis-selective (Sylvestre) Julia olefinations

Author keywords

Allenes; Julia olefination; Polyenes; Stereoselectivity

Indexed keywords

ALDEHYDE; ALLENE DERIVATIVE; BENZOTHIAZOLE; GAMMA ALLENYLALLYLBENZOTHIAZOLESULFONYL DERIVATIVE; POLYENE; SULFONE; UNCLASSIFIED DRUG;

EID: 13844269070     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-837214     Document Type: Article
Times cited : (36)

References (46)
  • 22
    • 0001186913 scopus 로고
    • Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Elsevier: Oxford, Chap. 3.4
    • Farina, V. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Elsevier: Oxford, 1995, Chap. 3.4, 161.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 161
    • Farina, V.1
  • 27
    • 13844257840 scopus 로고    scopus 로고
    • note
    • All new compounds gave satisfactory spectroscopic data and correct combustion analysis or HRMS.
  • 33
    • 0000546031 scopus 로고
    • Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford
    • Sharpless, K. B. In Comprehensive Organic Synthesis, Vol. 7; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 389-436.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 389-436
    • Sharpless, K.B.1
  • 40
    • 0345791431 scopus 로고    scopus 로고
    • (b) See for 12d: The sequence is provided below (Scheme 4); alternative preparation: Cole, K. P.; Hsung, R. P. Org. Lett. 2003, 5, 4843.
    • (2003) Org. Lett. , vol.5 , pp. 4843
    • Cole, K.P.1    Hsung, R.P.2
  • 42
    • 13844286316 scopus 로고    scopus 로고
    • manuscript in preparation
    • See for 12g: This vinylogous epoxy-retinal butenolide was acquired by inversion of the steps leading to the ring-deoxygenated peridinin skeleton (see ref. 11): Vaz, B.; Alvarez, R.; de Lera, A. R., manuscript in preparation. (diagram presented)
    • Vaz, B.1    Alvarez, R.2    De Lera, A.R.3
  • 43
    • 13844284526 scopus 로고    scopus 로고
    • note
    • max = 294, 416 nm (Figure 1). (diagram presented)
  • 44
    • 13844300392 scopus 로고    scopus 로고
    • note
    • -1 (Figure 2). (diagram presented)
  • 45
    • 13844303966 scopus 로고    scopus 로고
    • note
    • Determined by 2D HMQC-TOCSY. Although the geometry of 1,ω-bis(tributylstannyl)-1,3,5,7,9-decapentaene (16) reported by our group was in error (ref.9), the structures of the final carotenoids β,β-carotene and (3R,3′R)-zeaxanthin obtained by Stille coupling of 16 with the corresponding trienyliodides are correct. Isomerization takes place at the carotenoid stage by the action of palladium, since reagent 16 is stable to the Stille coupling reaction conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.