Diazomethane → HCID 21672634, compound

HRID 1420517Notes

Reaction equation

[CH3:1][C@H:2]1[C@H:30]([CH3:31])[C@@H:29]2[C@@:5]([C:33]([OH:35])=[O:34])([CH2:6][CH2:7][C@@:8]3([CH3:32])[C@:13]4([CH3:28])[CH2:14][CH2:15][C@H:16]5[C@@:21]([CH2:23][OH:24])([CH3:22])[C@@H:20]([OH:25])[C@H:19]([OH:26])[CH2:18][C@:17]5([CH3:27])[C@H:12]4[CH2:11][CH:10]=[C:9]32)[CH2:4][CH2:3]1.[N+](=[CH2:38])=[N-]>>[CH3:1][C@H:2]1[C@H:30]([CH3:31])[C@@H:29]2[C@@:5]([C:33]([O:35][CH3:38])=[O:34])([CH2:6][CH2:7][C@@:8]3([CH3:32])[C@:13]4([CH3:28])[CH2:14][CH2:15][C@H:16]5[C@@:21]([CH2:23][OH:24])([CH3:22])[C@@H:20]([OH:25])[C@H:19]([OH:26])[CH2:18][C@:17]5([CH3:27])[C@H:12]4[CH2:11][CH:10]=[C:9]32)[CH2:4][CH2:3]1

Participants

Reactant 2

HCID 9550Diazomethane

HCID 119034Asiatic Acid

Product 1

HCID 21672634HCID 21672634, compound

Procedure

Asiatic acid (2) is treated with diazomethane to obtain methyl asiatate (3, R3 =methyl) quantatively, which is then oxidized to give a compound of lactol structure (4, R3 =methyl) in which A-ring have been modified. The compound is treated with catalytic amount of acetic acid/piperidine to obtain methyl A(1)-norursa-2,12-diene-23-hydroxy-2-formyl-28-oate (5, R3 =methyl). [See Scheme 1]

Sources & evidence

ORD record: ord-74e04acb69a3454bb647c9d5a4cbec58
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06071898

Reaction notes

Loading…