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Volumn 43, Issue 20, 2002, Pages 3621-3624

Studies toward the total synthesis of garsubellin A: Synthesis of 8-deprenyl-garsubellin A

Author keywords

Cyclic carbonate; Garsubellin A; One pot reaction; Stille coupling; Tamao oxidation; Wacker type reaction

Indexed keywords

8 DEPRENYLGARSUBELLIN A; BICYCLO[3.3.1]NONANE 1,3,5 TRIONE; CARBONIC ACID; GARSUBELLIN A; HYDROXYL GROUP; KETONE DERIVATIVE; LACTONE; PHLOROGLUCINOL DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

EID: 0037071205     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)00650-0     Document Type: Article
Times cited : (60)

References (21)
  • 5
    • 0008927073 scopus 로고    scopus 로고
    • Deprotection of the acetonide was only possible at the enone stage (acetonide-protected 18-epi-6). The free 18-OH form (18-epi-6), however, could not be isolated due to the rapid intramolecular conjugate addition to the enone.
  • 6
    • 0008959759 scopus 로고    scopus 로고
    • note
  • 7
    • 0008904596 scopus 로고    scopus 로고
    • The relative configurations of lactones 8c and 13c were determined by converting to 27 (and the epimer) and comparing the NMR data with the compound obtained in the previous studies. Previously, the relative configuration of the compound was unequivocally determined based on X-ray crystallography.
  • 8
    • 0008892888 scopus 로고    scopus 로고
    • note
  • 9
    • 0008894597 scopus 로고    scopus 로고
    • iPrCO groups to avoid the repulsion between the solvated lithium atom of the enolate.
  • 12
    • 0008925490 scopus 로고    scopus 로고
    • The formation of the bicyclo[3.3.1] system in the presence of this silyl group was impossible due to the instability of the silicon.
  • 16
    • 0008949134 scopus 로고    scopus 로고
    • 2CuLi·LiCN gave unpredictable results.
  • 18
    • 0008904597 scopus 로고    scopus 로고
    • In the previous synthesis of 18-epi form, formation of the lactol corresponding to 23 was not significant.
  • 19
    • 0008925491 scopus 로고    scopus 로고
    • 3 as a base. In this case, however, these conditions gave a complex mixture of products.
  • 20
    • 0008903070 scopus 로고    scopus 로고
    • Undesired reduction of the vinyl iodide occurred in this step and 27 was obtained in 50% yield, which was then recycled to give an additional 13% of 2.
  • 21
    • 0008892018 scopus 로고    scopus 로고
    • +): 416.2563, found: 416.2568.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.