New synthesis of cortico steroids from 17-keto steroids: application and stereochemical study of the unsaturated sulfoxide-sulfenate rearrangement

Study on preparation of pregna‐4‐en‐17α,21‐diol‐3,20‐dione from androst‐4‐en‐3,17‐dione

“…This is an effective method that has the advantage of skipping protection step of the carbonyl functional groups at position C-3 and hydroxyl group at position C-17. [12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28] However, the final product is undesirable 17β-hydroxy pregnane isomer. Therefore, to furnish desire product, two additional steps of epimerization and hydration of 17β-ethynyl using the Kucherov reaction were required.…”

Steroids

“…Catalytic reduction of (152) followed by acid-catalyzed cyclization forms (153). A second catalytic hydrogenation produces the spirolactone (154). Direct oxidation of (154) yields diene (155).…”

“…In a similar industrial process, a mutant of Mycobacterium fortuitum degraded β-sitosterol to 9α-hydroxyandrosta-4-ene-3,17-dione [560-62-3] (105) (153). Dehydration of (105) to 9(11) -derivative (androsta-4,9-diene-3,17-dione [1035-69-4]) (106) provided starting material for corticosteroid synthesis (154). The rate of side-chain cleavage of sterols is limited by the low solubility of substrates and products and their low transport rates to and from cells.…”

Con đường mới tổng hợp 21‐acetoxypregn‐1,4,9(11)‐trien‐17α,21‐diol‐3,20‐dion

“…[1,2] Đã có nhiều công trình công bố tổng hợp cocticoid từ AD, 9α-OH AD. [3][4][5] Một trong số các giai đoạn quan trọng nhất tổng hợp cocticoid từ 17-ketosteroid là xây dựng mạch bên pregnan và tạo lập liên kết đôi-1 (2).…”