A new method has been developed for obtaining derivatives of 4β-/1'-alken-1'-yl/-2ξ;, 5a-dihydroxy-9,3aβ.4.5,8.8aβ-hexahydro-2H-cyclopenta [b] furane useful in the aynthesis of prostaglandins or their analogs, and a method for obtaining new sulphonyl starting compounds of the general formula 4, in which Z denotes a hydrogen atom or a protective group, Y denotes a group of the formula =CHOZ1, in which Z1 has the meaning stated for Z, whereby protective groups Z and Z1 may be the same or different, and Ar denotes optionally a substituted aryl group.
In the method according to the invention the new sulphonyl derivative of the general formula 4 is alkylated with an electrophilic agent comprising: carbonyl derivatives, oxiranes and halohydrins or their derivatives; the alkylation product is transformed into derivatives of 4β-1'-alken-1'-yl/ -2ξ, 5a-dihydroxy-3, 3aβ, 4,5,6,6aβ-hexahydro-2H-cyclopenta [b] furane in reactions which ensure obtaining a double bond C13 - C14.
New sulphonyl initial compounds of the general formula 4 are obtained from lactone of the general formula II, in which Z has the above stated meaning and L° denotes a leaving group, which is transformed into a sulphide; the obtained lactone-sulphide is reduced to lactol, and thereafter lactol-sulphide is oxidized to the sulphonyl derivative.
已开发出一种新方法,用于获得 4β-/1'-烯-1'-基/-2ξ;,5a-二羟基-9,3aβ.4.5,8.8aβ-六氢-2H-
环戊二烯[b]
呋喃用于合成
前列腺素或其类似物的方法,以及获得通式4的新磺酰基起始化合物的方法,其中Z表示氢原子或保护基,Y表示式=CHOZ1的基团,其中Z1具有Z的含义,保护基Z和Z1可以相同或不同,Ar表示任选取代的芳基。
在根据本发明的方法中,通式 4 的新磺酰基衍
生物与亲电剂烷基化,亲电剂包括:羰基衍
生物、
环氧乙烷和卤代烃或其衍
生物;烷基化产物在确保获得双键 C13 - C14 的反应中转化为 4β-1'-烯-1'-基/-2ξ,5a-二羟基-3,3aβ,4,5,6,6aβ-六氢-2H-环戊并[b]
呋喃的衍
生物。
通式 4 的新磺酰基初始化合物由通式 II 的内酯获得,其中 Z 具有上述含义,L° 表示离去基团,该离去基团被转化为
硫化物;获得的内酯-
硫化物被还原为乳醇,然后乳醇-
硫化物被氧化为磺酰基衍
生物。