Synthesis of -steganacin

Mont N, Mehta VP, Appukkuttan P et al (2008) Diversity oriented microwave-assisted synthesis of (-) -Steganacin aza-analogues. J Org Chem 73 7509-7516... 

SCHEME 125. Biomimetic synthesis of steganacin and related compounds... 

Optically pure l-(3, 4 -methylenedioxyphenyl)ethanol is a key chiral intermediate for the synthesis of Steganacin and Salmeterol. Apara-nitrobenzyl esterase cloned from Bacillus amyloliquefaciens (BAE) was employed to hydrolyze... 

This version of the Ullmann reaction was used for synthesis of bisbenzocyclo-octadiene lignans related to steganacin. Thus picrostegane (5) was synthesized as shown in equation(l). 

This reaction was a key step in the synthesis of the (+)-form of the dibenzocyclooctadiene lignan lactone steganacin (5).°... 

Steganacin.—A strategy for the synthesis of the antileukaemic lignan ( )-steganacin (17) has been discussed and put into practice by Raphael and his... 

Intramolecular photochemical dehydrohalogenation reactions have featured prominently in heterocyclic and carbocyclic synthesis. The novel photocyclization of the enamine (110) was the key reaction in the synthesis of the antileukaemic lignan steganacin (111) (Scheme 36). This cyclization could have occurred by the SrnI mechanism. ... 

Ring-expansions by use of acetylene dicarboxylates (ADC) in cycloadditions are well known and nicely examplihed in the conversion of the enamine (34) into the dibenzo-cot (35). A fascinating application of this reaction to the synthesis of the anti-leukaemic lignan steganacin (36) has been published. The marine natural product caulerpin, previously reported as a dinaphthopyrazine derivative, has now been shown to be the bis-indolo-cyclo-octatetraene (37), both by... 

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