Asymmetric Total Synthesis of Attenol A and B

Synlett

Volumn , Issue 14, 2003, Pages 2185-2187

  Enders, Dieter ^a   Lenzen, Achim ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Asymmetric dihydroxylation; Dithianes; Natural products; SAMP hydrazone methodology; Total synthesis

Indexed keywords

ATTENOL A; ATTENOL B; HYDRAZONE DERIVATIVE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DIHYDROXYLATION; DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0242408211     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42071     Document Type: Article

References (30)

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9. For reviews about the SAMP/RAMP-hydrazone methodology in asymmetric synthesis see: (a) Enders, D. In Asymmetric Synthesis, Vol. 3; Morrison, J. D., Ed.; Academic Press: Orlando, 1984, 275. (b) Job, A.; Janeck, C. F.; Bettray, W.; Peters, R.; Enders, D. Tetrahedron 2002, 58, 2253.
10. For reviews about the SAMP/RAMP-hydrazone methodology in asymmetric synthesis see: (a) Enders, D. In Asymmetric Synthesis, Vol. 3; Morrison, J. D., Ed.; Academic Press: Orlando, 1984, 275. (b) Job, A.; Janeck, C. F.; Bettray, W.; Peters, R.; Enders, D. Tetrahedron 2002, 58, 2253.
11. Compound 6 is a versatile chiral dihydroxy acetone dicarbanion equivalent. For its applications see: (a) Enders, D.; Bockstiegel, B. Synthesis 1989, 493. (b) Enders, D.; Gatzweiler, W.; Jegelka, U. Synthesis 1991, 1137. (c) Enders, D.; Jegelka, U. Synlett 1992, 999.
12. Compound 6 is a versatile chiral dihydroxy acetone dicarbanion equivalent. For its applications see: (a) Enders, D.; Bockstiegel, B. Synthesis 1989, 493. (b) Enders, D.; Gatzweiler, W.; Jegelka, U. Synthesis 1991, 1137. (c) Enders, D.; Jegelka, U. Synlett 1992, 999.
13. Compound 6 is a versatile chiral dihydroxy acetone dicarbanion equivalent. For its applications see: (a) Enders, D.; Bockstiegel, B. Synthesis 1989, 493. (b) Enders, D.; Gatzweiler, W.; Jegelka, U. Synthesis 1991, 1137. (c) Enders, D.; Jegelka, U. Synlett 1992, 999.
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28. The reaction sequence leading to 15 was also conducted starting with 5 of much lower enantiomeric purity (i.e. ee = 83%). After HPLC, 15 (obtained in lower yield) was still diastereomerically and enantiomerically pure (de, ee ≥ 98%) which indicates the high stereoselectivity of the Sharpless asymmetric dihydroxylation.
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30. 3) for natural 2}. All new compounds gave satisfactory spectral data and correct elemental analyses.