| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345600 | Tetrahedron: Asymmetry | 2016 | 6 Pages |
The total synthesis of (−)-conduramine A-1 was achieved by using a diastereomerically enriched syn,anti-oxazine intermediate. The key steps in this strategy were the stereoselective extension of the chirality of syn,anti-oxazine, a Wittig reaction, and a ring-closing metathesis reaction.
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(S)-1-((4R,5S,6R)-5-((tert-Butyldimethylsilyl)oxy)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2-phenyl-5,6-dihydro-4H-1,3-oxazin-6-yl)prop-2-en-1-olC26H45NO4Si2[α]D25 = +16.1 (c 0.5, CHCl3)Source of chirality: From d-serine and asymmetric synthesisAbsolute configuration: (S)-1-(4R,5S,6R)
(R)-1-((4R,5S,6R)-5-((tert-Butyldimethylsilyl)oxy)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2-phenyl-5,6-dihydro-4H-1,3-oxazin-6-yl)prop-2-en-1-olC26H45NO4Si2[α]D25 = +29.1 (c 0.23, CHCl3)Source of chirality: From d-serine and asymmetric synthesisAbsolute configuration: (R)-1-(4R,5S,6R)
(S)-1-((4R,5S,6R)-5-((tert-Butyldimethylsilyl)oxy)-4-(((tert-butyldimethylsilyl)oxy)methyl)-2-phenyl-5,6-dihydro-4H-1,3-oxazin-6-yl)allyl acetateC28H47NO5Si2[α]D25 = +35.4 (c 0.6, CHCl3)Source of chirality: From d-serine and asymmetric synthesisAbsolute configuration: (S)-1-((4R,5S,6R)
(3S,4R,5S,6R)-3-Acetoxy-6-(((benzyloxy)carbonyl)amino)-5,7-bis((tert-butyldimethylsilyl)oxy)hept-1-en-4-yl benzoateC36H55NO8Si2[α]D25 = −2.6 (c 0.6, CHCl3)Source of chirality: From d-serine and asymmetric synthesisAbsolute configuration: (3S,4R,5S,6R)
(3S,4R,5S,6R)-3-Acetoxy-6-(((benzyloxy)carbonyl)amino)-5-((tert-butyldimethylsilyl)oxy)-7-hydroxyhept-1-en-4-yl benzoateC30H41NO8Si[α]D25 = −100.0 (c 0.3, CHCl3)Source of chirality: From d-serine and asymmetric synthesisAbsolute configuration: (3S,4R,5S,6R)
(3S,4R,5S,6R,E)-3-Acetoxy-6-(((benzyloxy)carbonyl)amino)-5-((tert-butyldimethylsilyl)oxy)-8-phenylocta-1,7-dien-4-ylC37H45NO7Si[α]D25 = −15.1 (c 0.6, CHCl3)Source of chirality: From d-serine and asymmetric synthesisAbsolute configuration: (3S,4R,5S,6R)
(3S,4R,5S,6R,Z)-3-Acetoxy-6-(((benzyloxy)carbonyl)amino)-5-((tert-butyldimethylsilyl)oxy)-8-phenylocta-1,7-dien-4-yl benzoateC37H45NO7Si[α]D25 = +67.1 (c 0.8, CHCl3)Source of chirality: From d-serine and asymmetric synthesisAbsolute configuration: (3S,4R,5S,6R)
(1R,2S,5R,6R)-2-Acetoxy-5-(((benzyloxy)carbonyl)amino)-6-((tert-butyldimethylsilyl)oxy)cyclohex-3-en-1-yl benzoateC29H37NO7Si[α]D25 = +100.0 (c 0.6, CHCl3)Source of chirality: From d-serine and asymmetric synthesisAbsolute configuration: (1R,2S,5R,6R)
(1R,2R,3S,6R)-6-Aminocyclohex-4-ene-1,2,3-triolC6H11NO3[α]D25 = −18.8 (c 0.86, MeOH)Source of chirality : From d-serine and asymmetric synthesisAbsolute configuration : (1R,2S,5R,6R)
