49686-55-7

Usage

Uses

Used in Pharmaceutical Industry:
(1S,3aR)-1,5,6,8,9,14bβ-Hexahydro-2-methoxy-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepine-1α,9α-diol is used as a potential pharmaceutical candidate for various applications due to its complex structure and specific stereochemistry. Its unique molecular features may contribute to its potential as a therapeutic agent or as a building block for the development of new drugs.
Used in Chemical Research:
(1S,3aR)-1,5,6,8,9,14bβ-Hexahydro-2-methoxy-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepine-1α,9α-diol is used as a subject of chemical research to explore its properties, reactivity, and potential applications. (1S,3aR)-1,5,6,8,9,14bβ-Hexahydro-2-methoxy-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepine-1α,9α-diol's intricate structure and stereochemistry make it an interesting target for studies aimed at understanding its behavior and interactions with other molecules.
Used in Material Science:
(1S,3aR)-1,5,6,8,9,14bβ-Hexahydro-2-methoxy-4H-cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepine-1α,9α-diol may be used in material science for the development of new materials with specific properties. Its unique molecular structure and functional groups could contribute to the creation of materials with tailored characteristics for various applications, such as sensors, catalysts, or advanced materials with specific mechanical, electrical, or optical properties.

InChI:InChI=1/C18H21NO5/c1-22-15-7-18-3-2-4-19(18)8-12(20)10-5-13-14(24-9-23-13)6-11(10)16(18)17(15)21/h5-7,12,16-17,20-21H,2-4,8-9H2,1H3/t12-,16+,17+,18-/m0/s1

Upstream product

• 130553-02-5 (3aS*,9β)-(+/-)-9-acetoxycephalotaxin-1-one 
• 32345-76-9 (R)-(-)-2-(3,4-methylenedioxyphenyl)-2-hydroxyacetic acid 
• 952251-70-6 1-aza-spiro[4.4]non-6-ene 
• 180413-05-2 1-(Toluene-4-sulfonyl)-1-aza-spiro[4.4]non-6-ene 
• 2910-66-9 3-cyclopent-1-enylpropionic acid ethyl ester 
• 2910-67-0 3-cyclopent-1-enyl-propionic acid 
• 2910-59-0 3-(cyclopent-1-en-1-yl)propan-1-ol 
• 952251-84-2 C₈H₁₁ON 
• 952251-82-0 C₈H₁₃ON 
• 952252-14-1 C₁₉H₁₉O₆N 
• 952252-12-9 C₁₉H₂₃O₆N 
• 952252-10-7 C₁₉H₂₁O₄N 
• 952252-08-3 C₁₉H₁₉O₆N 
• 952252-06-1 C₁₉H₂₃O₆N 

Downstream Products

• 24268-97-1 (+/-)-drupacine 
• 24268-96-0 3,11-O,O-Diacetylhydroxycephalotaxin 
• 24268-98-2 3-O-Acetyldrupacin 
• 24268-96-0 (3aR)-1t,9c-diacetoxy-2-methoxy-(3arC⁴,14bc)-1,5,6,8,9,14b-hexahydro-4H-cyclopenta[b][1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepine 
• 49686-61-5 11-hydroxycephalotaxinone hemiketal 
• 49686-57-9 (-)-drupacine 

Relevant academic research and scientific papers

Collective Asymmetric Total Synthesis of C-11 Oxygenated Cephalotaxus Alkaloids

While numerous studies pertaining to the total synthesis of Cephalotaxus alkaloids have been reported, only two strategies have been reported to date for the successful synthesis of the C-11 oxygenated subset, due to the additional synthetic challenge posed by the remote C-11 stereocenter. Herein, we report the collective asymmetric total synthesis of C-11 oxygenated Cephalotaxus alkaloids using a chiral proline both as a starting material and as the only chirality source. A tetracyclic advanced intermediate was synthesized in a highly stereoselective manner from l-proline in 8 steps involving sequential chirality transfer steps such as a diastereoselective N-alkylation, stereospecific Stevens rearrangement and intramolecular Friedel–Crafts reaction via an unusual O-acyloxocarbenium intermediate. From a common intermediate, the asymmetric total synthesis of six C-11 oxygenated Cephalotaxus alkaloids was completed by a series of oxidation state adjustments.

Convergency and divergency as strategic elements in total synthesis: The total synthesis of (-)-drupacine and the formal total synthesis of (±)-cephalotaxine, (-)-cephalotaxine, and (+)-cephalotaxine

(Chemical Equation Presented) A concise route toward the syntheses of (-)-drupacine and (+)- and (-)-cephalotaxine has been developed. The syntheses rely on Pd(II)-catalyzed aerobic oxidative heterocyclization chemistry, which was employed to rapidly cons

Total synthesis of the Cephalotaxus alkaloids dl-cephalotaxine, dl-11-hydroxycephalotaxine, and dl-drupacine

This paper reports the chemical details of our total synthesis of dl-cephalotaxine (1) and the completion of the first total synthesis of dl-11-hydroxycephalotaxine (3) and dl-drupacine (4). Key steps in the synthesis of dl-cephalotaxine include: (1) conj