1402069-89-9

Upstream product

• 654061-13-9 (R)-4-(7-methoxybenzo[1,3]dioxol-5-yl)but-3-en-2-ol 
• 1402069-91-3 C₁₉H₂₅NO₇ 
• 1402069-79-7 (2R,3R,E)-Methyl 2-(tert-butoxycarbonylamino)-3-(7-methoxybenzo[d]-ACHTUNGTRENUNG[1,3]dioxol-5-yl)hex-4-enoate 
• 1402069-82-2 tert-butyl (1R,6R)-2-(benzyloxy)-6-(7-methoxybenzo[d][1,3]dioxol-5-yl)-4-oxocyclohex-2-enylcarbamate 
• 1402069-80-0 (2R,3R)-methyl 2-(tert-butoxycarbonylamino)-3-(7-methoxybenzo[d][1,3]dioxol-5-yl)-5-oxohexanoate 
• 4530-20-5 BOC-glycine 

Relevant academic research and scientific papers

Total synthesis of (+)-trans- dihydronarciclasine from (+)-7-azabicyclo[2.2.1]heptanone

A concise asymmetric total synthesis of Amaryllidaceae alkaloid (+)-trans-dihydronarciclasine is accomplished starting from optically pure 7-azabicyclo[2.2.1]heptanone scaffold in 13 linear steps. Key features of the strategy include substrate-directed st

Stereocontrolled total synthesis of (+)-trans-dihydronarciclasine

A highly stereoselective and efficient total synthesis of trans-dihydronarciclasine from a readily available chiral starting material was developed. The synthesis defines two of the five stereogenic centers of the natural product by an amino acid ester-enolate Claisen rearrangement. The other three stereogenic centers are created in a highly stereocontrolled fashion via a six-ring vinylogous ester intermediate, which is generated from the γ,δ-unsaturated ester functional group of the Claisen rearrangement product in an efficient three-step sequence. This concise total synthesis exemplifies the use of a highly regioselective Friedel-Crafts-type cyclization to form the B ring via an isocyanate intermediate derived from an N-Boc group, which is superior to the conventional method using an imino triflate intermediate. This same N-Boc group is employed to give high selectivity in the Claisen rearrangement earlier in the sequence. A highly selective and efficient total synthesis of (+)-trans-dihydronarciclasine was developed. The synthesis defines two of the five stereocenters in an amino acid ester-enolate Claisen rearrangement. The other three stereocenters are created via a cyclic vinylogous ester intermediate, which was generated from the γ,δ-unsaturated ester functional group of the rearrangement product. The B ring is constructed by a Friedel-Crafts-type cyclization, exemplifying the use of an N-Boc group to generate an isocyanate intermediate (see scheme). Copyright