کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
2028564 1070426 2010 7 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Unusual oxidative transformations of a steroidal 16α,17α,22-triol
موضوعات مرتبط
علوم زیستی و بیوفناوری بیوشیمی، ژنتیک و زیست شناسی مولکولی زیست شیمی
پیش نمایش صفحه اول مقاله
Unusual oxidative transformations of a steroidal 16α,17α,22-triol
چکیده انگلیسی

A number of unexpected reactions were observed during attempts to invert configuration at C16 in 16α,17α,22-triol 3a. The PDC oxidation of 3a produced the D-seco-aldehyde 4a. Analogous compound 4b was obtained by Swern oxidation of the 16α,17α-dihydroxy-22-O-TES-ether 3b in addition to the desired 16-ketone 7. The unprotected triol 3a yielded pentacyclic products 5 and 6 under similar conditions. The Mitsunobu reaction of the triol 3a afforded 16-ketone 8 with inverted configuration of the side chain. During heating of a solution of 3a in THF with NaH at reflux autoxidation to the 16-ketone cyclic hemiketal 5, identical to one of the Swern oxidation products, took place.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Steroids - Volume 75, Issue 1, January 2010, Pages 70–76
نویسندگان
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