23599-45-3

Usage

InChI:InChI=1/C17H24O5/c1-11(20)22-13-8-12(9-18)17(21,10-19)16(4)7-5-6-15(2,3)14(13)16/h8-10,13-14,21H,5-7H2,1-4H3/t13-,14+,16+,17-/m1/s1

Upstream product

• 108-24-7 acetic anhydride 
• 174173-34-3 KT-7766 
• 127681-52-1 6-β-acetoxy-7-drimen-9α,11,12-triol 
• 78424-45-0 6β-hydroxywarburganal 
• 78424-40-5 trans-4,5,5a,6,7,8,9,9a-octahydro-5-oxo-6,6,9a-trimethyl-naphtho<1,2-c>furan 
• 73879-08-0 Acetic acid (1R,4R,4aS,8aS)-3-[1,3]dioxan-2-yl-4-formyl-4-hydroxy-4a,8,8-trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester 
• 71557-91-0 9α,11-carbonyldioxydrim-7-en-12-ol 
• 73879-05-7 C₁₈H₂₄O₆ 
• 127681-60-1 7-drimen-6β,9α,11-triol 11-O-tert-butyldimethylsilyl ether 
• 110547-82-5 6-oxo-7-drimen-11-ol acetate 
• 173991-53-2 KT-7620 
• 74411-45-3 C₂₁H₂₇Cl₃O₈ 
• 74411-43-1 C₁₉H₂₃Cl₃O₇ 
• 74411-44-2 C₁₉H₂₅Cl₃O₇ 

Downstream Products

• 16772-63-7 (-)-pereniporin B 

Relevant academic research and scientific papers

RES-1149-1 and -2, novel non-peptidic endothelin type B receptor antagonists produced by Aspergillus sp. II. Structure determination and derivatization

The structures of two novel non-peptidic endothelin type B receptor antagonists, RES-1149-1 and -2 were determined by spectroscopic methods. Several derivatives were synthesized from RES-1149-1 for biological assay.

SYNTHETIC STUDIES ON BIOLOGICALLY ACTIVE NATURAL COMPOUNDS. PART I: STEREOSPECIFIC TRANSFORMATION OF UVIDIN A INTO (-)-CINNAMODIAL

A partial synthesis of (-)-cinnamodial (1) has been achived, using (+)-uvidin A (3) as starting material.This also represents a formal synthesis of (-)-cinnamosmolide (2a) and pereniporin B (2b).

Syntheses of the Insect Antifeedant (+/-)-Cinnamodial and the Drimane Sesquiterpenoids (+/-)-Isodrimenin and (+/-)-Fragrolide

Total syntheses of (+/-)-cinnamodial (5), (+/-)-isodrimenin (24), and (+/-)-fragrolide (29) are described begining from the diene 7.Hydroboration-oxidation of 7 gave the trans-fused alcohol 18, and elimination of mesylate 21, followed by selective reduction at the more accesible ester function, led to γ-lactone 23, which afforded 24 upon hydrogenation.A different route from 18 produced triol 27, which was selectively oxidized at the more exposed primary alcohol to yield γ-lactone 28.The latter, upon oxidation, furnished 29.The synthesis of 5 hinged upon the construction of furan 38 , which was obtained from lactone 26 via 37 or, directly, by oxidation of 27.Oxidation of 38 with lead tetraacetate gave 41, which underwent elimination with DBU to provide 43.Regio- and stereoselective epoxidation of this dienone gave 45 which, upon acidic methanolysis, led to 50.Reduction of this ketone resulted in the 6β alcohol 51, and exposure of this bis acetal to acid released the dialdehyde array of 52.Finally, acetylation of 52 gave 5.

SYNTHESES OF (+/-)-CINNAMODIAL AND (+/-)-CINNAMOSMOLIDE

Syntheses of (+/-)-cinnamodial and (+/-)-cinnamosmolide were achieved starting from the intermediate used in the synthesis of (+/-)-warburganal.