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Extra info for Bioactive Natural Products Part L
BnBr, Ag2O, TBAI OTBS 2. TBDMSOTf 3. LiAIH4 3. HCI OBn OBn OBn 84 85 ,Ar NaBH 4 [ OH T ) ~ CH2OH 1. Jones ox 2. CICO2Et; then BnO,,,, 3. 90 °C, PhMe; then MeOH ""Cfy 4. LiAIK. 87 ,Ar (47%, four steps) OH 88 ^Ar 1. (Boc) 2 O 2. H 2 , Pd(OH)2 BnO,,, 3>-N(Boc)Me 3. (BnO)2PN(/Pr)2 4. f-BuOOH OP(OXOBn)2 89 (3R)-isomer 48 (3S)-isomer Scheme 27. Brummond's formal synthesis of FR901483 ^ FR901483 mMe 32 configuration of a C(3) was not established, the synthesis was continued with both isomers of 87. At this point, to complete the synthesis of advanced intermediate 48 and hence FR901483 itself, the elaboration of the methylamino group at C(3) remained.
Catalytic hydrogenolysis of 125 and subsequent treatment with DBU gave azaspirocycle 121. Construction of the piperazine ring commences with alkylation of the secondary amine using ethyl bromoacetate, desilylation of the protected alcohol and conversion of the hydroxyl into the azido group  to provide 126. Hydrogenolysis of the azide and hydrolysis of the ester led to amino acid 120. Treatment of the latter with DPPA  afforded the desired piperazine, which was methylated to yield 119. Aldol reaction of the enolate of lactam 119 and 4-(3-methyl-but-2enyloxy)-benzaldehyde  provided a mixture of two separable alcohols 127.
In this synthesis the introduction of the side chain upon the carbocyclic ring was carried out by an aldol condensation between the aldehyde 80 and the monoacetal of 1,4-cyclohexanedione. Treatment of the latter with LDA, followed by addition of 80 resulted in the formation of aldol 81 as the major diastereoisomer (42%). Reduction of [3-hydroxy ketone 81 with NaBH4 stereoselectively afforded diol 82, which was diprotected with benzyl bromide. The Boc group was then chemoselectively removed using a two-step sequence to give 83.