Stereodivergent synthesis of (-)- and (+)-slaframine from γ-hydroxy- α,β-unsaturated sulfones

Synlett

Volumn , Issue 1, 1999, Pages 49-52

  Carretero, Juan C ^a   Gómez Arrayás, Ramón ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Indolizidine; Intramolecular conjugate addition; Pyrrolidine; Slaframine; , unsaturated sulfone

Indexed keywords

SLAFRAMINE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; STRUCTURE ANALYSIS;

EID: 0344572790     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2546     Document Type: Article

References (30)

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23. 2,3-trans ∼2.5 Hz); see refs. 5 and 9.
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26. 3Al, it seemed plausible that in the case of 6a the formation of the required starting chelate would be hampered by severe steric interactions between the acetonide and sulfonylmethyl groups. As it is shown in the figures below, both substituents would be placed on the same face of the pyrrolidine in the chelate coming from 6a, whereas they would be on opposite faces in the chelate formed from 6b. (Formula presented)
27. 5SSi: C, 61.44; H, 9.36; N, 2.65. Found; C, 61.56; H, 9.37; N, 2.45.
28. Eluting with hexane/i-PrOH mixture, 90:10 v/v, 1.0 ml/min; retention times of 5.4 min and 6.3 min for both enantiomers of (±)-7, which was prepared from (±)-glyceraldehyde acetonide following the reactions shown in scheme 2.
29. 5ax,6 (see figures below).
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