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Volumn 62, Issue 41, 2006, Pages 9641-9649

Enantioselective synthesis and absolute configurations of aculeatins A, B, D, and 6-epi-aculeatin D

Author keywords

Absolute configuration; Aculeatins; Aldol reaction; Asymmetric allylation; Hypervalent iodine; Oxidative spiroacetalization; Remote induction; Spiroacetals

Indexed keywords

6 EPIACULEATIN D; ACETAL DERIVATIVE; ACULEATIN A; ACULEATIN B; ACULEATIN D; UNCLASSIFIED DRUG;

EID: 33748034030     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.07.076     Document Type: Article
Times cited : (41)

References (43)
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    • The aldol addition step of the enolborane of β-alkoxy methyl ketone 8 to n-tetradecanal takes place with complete stereoselectivity, which reflects a high anti-1,5-induction. This remote induction was previously observed by other groups in related cases:
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    • Spirocyclic amino compounds can also be prepared with this oxidative methodology. See:
    • Spirocyclic amino compounds can also be prepared with this oxidative methodology. See:. Canesi S., Belmont P., Bouchu D., Rousset L., and Ciufolini M.A. Tetrahedron Lett. 43 (2002) 5193-5195
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    • note
    • The way of drawing the aculeatins in Ref. 1 is confusing, as two spiro connected rings are simultaneously used as reference rings for stereochemical representation. We prefer the way depicted in Figure 1, where only the tetrahydropyran moiety is used as the reference ring.
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    • note
    • The sensitivity of the β-oxygenated ketone moiety in 18 toward acidic or basic reagents was a concern here.
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    • This behavior is well precedented:
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    • note
    • Freshly prepared by PCC oxidation of n-tetradecanol.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.