20-Hydroxyecdysone → Ponasterone A

HRID 43304Notes

Reaction equation

[CH3:1][C@@:2]12[C@@H:22]([C@@:23]([OH:33])([C@H:25]([OH:32])[CH2:26][CH2:27][C:28]([OH:31])([CH3:30])[CH3:29])[CH3:24])[CH2:21][CH2:20][C@@:19]1([OH:34])[C:6]1=[CH:7][C:8]([C@@H:10]3[CH2:15][C@@H:14]([OH:16])[C@@H:13]([OH:17])[CH2:12][C@:11]3([CH3:18])[C@H:5]1[CH2:4][CH2:3]2)=[O:9].[CH3:35][C@@:36]12[C@@H:56]([C@@:57]([OH:67])([C@H:59]([OH:66])[CH2:60][CH2:61][C:62](O)([CH3:64])[CH3:63])[CH3:58])[CH2:55][CH2:54][C@@:53]1([OH:68])[C:40]1=[CH:41][C:42]([C@@H:44]3[CH2:49][C@@H:48]([OH:50])[C@@H:47]([OH:51])[CH2:46][C@:45]3([CH3:52])[C@H:39]1[C@H:38](O)[CH2:37]2)=[O:43]>>[CH3:1][C@@:2]12[C@@H:22]([C@@:23]([OH:33])([C@H:25]([OH:32])[CH2:26][CH2:27][C:28]([OH:31])([CH3:29])[CH3:30])[CH3:24])[CH2:21][CH2:20][C@@:19]1([OH:34])[C:6]1=[CH:7][C:8]([C@@H:10]3[CH2:15][C@@H:14]([OH:16])[C@@H:13]([OH:17])[CH2:12][C@:11]3([CH3:18])[C@H:5]1[CH2:4][CH2:3]2)=[O:9].[CH3:64][CH:62]([CH2:61][CH2:60][C@@H:59]([OH:66])[C@:57]([OH:67])([C@@H:56]1[C@@:36]2([CH3:35])[CH2:37][CH2:38][C@@H:39]3[C@@:45]4([CH3:52])[CH2:46][C@H:47]([OH:51])[C@H:48]([OH:50])[CH2:49][C@H:44]4[C:42](=[O:43])[CH:41]=[C:40]3[C@:53]2([OH:68])[CH2:54][CH2:55]1)[CH3:58])[CH3:63]

Participants

Reactant 2

HCID 545984020-Hydroxyecdysone

HCID 14376672Turkesterone

Product 2

HCID 115127Ponasterone A

HCID 545984020-Hydroxyecdysone

Procedure

Semi-synthetic steroids 20E 2-methyl ether, 20E 3-methyl ether, 20E 22-methyl ether, 20E 2,22-dimethyl ether, 20E 3,33-dimethyl ether, 20E 2,3,14,22-tetramethyl ether, 20-hydroxyecdysone 22-O-pyrrole carboxylate, and turkesterone-11 alpha propionate, turkesterone-11 alpha hexanoate, turkesterone-11 alpha decanoate were prepared from 20E or turkesterone. The remaining steroids were isolated from plant materials, except for ponasterone A which was also synthesised from 20-hydroxyecdysone. Muristerone A which was purchased by AG Scientific Inc (San Diego, Calif.). The following compounds were generously supplied by other researchers: 2-deoxyecdysone, ecdysone, 2-deoxy-20-hydroxyecdysone, and cyasterone (Prof. René Lafont), taxisterone, polypodine B, ajugasterone C, (25S)-inokosterone, (25R)-inokosterone, makisterone A, makisterone C, carthamosterone, intergristerone A (Dr. Juraj Harmatha), 20-hydroxyecdysone (Dr. Vladimir Volodin), turkesterone (Prof. Zyadilla Saatov) and canescensterone (Prof. Apichart Suksamram). Reagents and solvents used for the synthesis/purification were purchased from Fisher Scientific and Sigma-Aldrich. Water for HPLC was deionized to a degree of purity of 17 W.

Sources & evidence

ORD record: ord-384567abaaa642179facb61d2dfc25f1
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536354B2

Reaction notes

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