137664-63-2

Upstream product

• 25581-41-3 D-erythronolactone acetonide 
• 2393-23-9 4-methoxy-benzylamine 
• 138253-24-4 (S)-1-(4-Methoxy-benzyl)-5-(4-methoxy-benzyloxymethyl)-pyrrolidin-2-one 
• 138253-26-6 (S)-1-(4-Methoxy-benzyl)-5-methoxymethyl-1,5-dihydro-pyrrol-2-one 
• 138253-25-5 (S)-1-(4'-methoxybenzyl)-5-methoxymethyl-pyrrolidin-2-one 
• 152500-26-0 (S)-5-(hydroxymethyl)-1-(4-methoxyphenylmethyl)-2-pyrrolidinone 
• 254442-10-9 (3aR,6R,6aR)-5-(4-Methoxy-benzyl)-6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one 
• 254892-77-8 (3aR,3bR,6R,8aR)-2,2-Dimethyl-6-phenyl-tetrahydro-[1,3]dioxolo[4',5':3,4]pyrrolo[1,2-c]oxazol-8-one 
• 254441-91-3 (3aR,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one 
• 17342-08-4 (S)-Pyroglutaminol 
• 137664-61-0 (3aR,6R,6aR)-6-(3,3-Dimethyl-2-oxo-butyl)-5-(4-methoxy-benzyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one 
• 137664-60-9 Acetic acid (3aS,6aR)-5-(4-methoxy-benzyl)-2,2-dimethyl-6-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl ester 
• 137664-59-6 (3aR,6aS)-6-Hydroxy-5-(4-methoxy-benzyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one 
• 137664-58-5 (4R,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 4-methoxy-benzylamide 

Downstream Products

• 137664-66-5 (3aR,6R,6aR)-5-(4-Methoxy-benzoyl)-6-methoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one 
• 137683-86-4 (3aR,6R,6aR)-6-Methoxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one 
• 137664-64-3 [(R)-1-((4R,5R)-5-{(R)-3-[4-(tert-Butyl-diphenyl-silanyloxymethyl)-oxazol-2-yl]-butylcarbamoyl}-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-ethyl]-carbamic acid tert-butyl ester 
• 138253-28-8 [(R)-1-((4R,5R)-5-Benzylcarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-ethyl]-carbamic acid tert-butyl ester 
• 138253-29-9 (4R,5R)-5-((R)-1-Dimethylamino-2-methoxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzylamide 

Relevant academic research and scientific papers

Total synthesis of (+)-calyculin A and (-)-calyculin B: Cyanotetraene construction, asymmetric synthesis of the C(26-37) oxazole, fragment assembly, and final elaboration

A convergent total synthesis leading to (+)-calyculin A and (-)-calyculin B (1 and 2), antipodes of the potent, highly selective and remarkably cell-permeable phosphatase inhibitors calyculins A and B, has been achieved. In the preceding paper we outlined the asymmetric synthesis of the C(9-25) spiroketal dipropionate subunit (+)-BC; herein we describe construction of the C(1-8) cyanotetraene, an asymmetric synthesis of the C(26-37) oxazole, fragment assembly and final elaboration to (+)-1 and (-)-2. Highlights of the synthesis include: application of a one-pot three-component Suzuki reaction for the construction of phosphonate A, a bifunctional triene precursor of the light sensitive C(1-8) cyanotetraene subunit, an asymmetric synthesis of the C(26-32) oxazole (-)-D, exploiting the Silks-Odom 77Se NMR protocol to assess enantiomeric purity, construction of the C(33-37) subtarget (-)-E in a highly stereocontrolled fashion via an acyliminium ion, and a concise, highly efficient sequence for fragment assembly and elaboration to (+)-calyculin A and (-)-calyculin B. The synthesis of (-)-2 also confirms the structure of calyculin B, previously based only on spectral comparison with calyculin A.

Calyculin synthetic studies. 2. Stereocontrolled assembly of the C(9)-C(13) dithiane and C(26)-C(37) oxazole intermediates

The C(9)-C(13) dithiane (+)-2 and C(26)-C(37) γ-amino acid/oxazole (+)-5, key building blocks for calyculin total synthesis, have been elaborated in homochiral form. Noteworthy features of the schemes include stereocontrolled generation of the C(36) steeo

Stereoselective Synthesis of 2,3-Dihydroxy-4-dimethylamino-5-methoxypentanoic Acid, A Fragment of Calyculins - Determination of the Absolute Configuration of Calyculins

2,3-Dihydroxy-4-dimethylamino-5-methoxypentanoic acid (2) with (2R,3R,4R)-configuration has been stereoselectively prepared from (S)-pyroglutaminol (3) and revealed to be the enantiomer of the compound derived from calyculins (1), which provides the conclusicve evidence on the absolutr configuration of calyculins.