Total Syntheses of (−)-Spirooliganones A and B

The enantioselective syntheses of (−)-spirooliganones A and B have been accomplished in eight steps from commercially available starting materials. Noteworthy transformations include a three-component hetero-Diels–Alder cycloaddition to construct the tetracyclic core of spirooliganones, a Sharpless asymmetric dihydroxylation, and a tandem oxidative dearomatization/cyclization to build the oxa-spiro cyclohexadienone skeleton. The straightforward syntheses were performed without protecting groups

Cu/Mn Co-oxidized Cyclization for the Synthesis of Highly Substituted Pyrrole Derivatives from Amino Acid Esters: A Strategy for the Biomimetic Syntheses of Lycogarubin C and Chromopyrrolic Acid

An effective and concise approach to synthesis of tetrasubstituted pyrroles from readily available amino acid esters by the promotion of Cu­(OAc)2 in conjunction with Mn­(OAc)3 has been developed. This reaction proceeds through multiple dehydrogenations, deamination, and oxidative cyclization. This oxidized system tolerates substrates bearing various electron-donating or electron-withdrawing groups. With this methodology, several key intermediates of natural products have been effectively prepared, and the total syntheses of lycogarubin C and chromopyrrolic acid have been completed in high efficiency

Cu/Mn Co-oxidized Cyclization for the Synthesis of Highly Substituted Pyrrole Derivatives from Amino Acid Esters: A Strategy for the Biomimetic Syntheses of Lycogarubin C and Chromopyrrolic Acid

An effective and concise approach to synthesis of tetrasubstituted pyrroles from readily available amino acid esters by the promotion of Cu­(OAc)₂ in conjunction with Mn­(OAc)₃ has been developed. This reaction proceeds through multiple dehydrogenations, deamination, and oxidative cyclization. This oxidized system tolerates substrates bearing various electron-donating or electron-withdrawing groups. With this methodology, several key intermediates of natural products have been effectively prepared, and the total syntheses of lycogarubin C and chromopyrrolic acid have been completed in high efficiency

Asymmetric Total Syntheses of <i>ent</i>-Stachybotrin C and Its Congener

The asymmetric total syntheses of ent-stachybotrin C and its congener have been accomplished through a convergent approach in the longest linear sequence of 12 steps from commercially available materials, respectively. Noteworthy transformation of the synthesis involved a cascade Knoevenagel condensation/Hantzsch ester reduction/epoxide ring-opening/transetherification to construct the core pyran ring with two adjacent stereocenters

An Efficient Synthesis of Highly Functionalized [5,6] Aromatic Spiroketals by Hetero-Diels−Alder Reaction

A hetero-Diels−Alder reaction of vinyl sulfoxides with o-quinone methides precursor constructs highly functionalized [5,6] aromatic spiroketal skeletons in moderate to good yields with high regioselectivity. The two functional groups (ketone and olefin) can be further subjected to many synthetic transformations

Correction to “Biomimetic Total Synthesis of Paeoveitol”

Correction to “Biomimetic Total Synthesis of Paeoveitol

Synthetic Study of Rubriflordilactone B: Highly Stereoselective Construction of the C‑5-epi ABCDE Ring System

A highly stereocontrolled construction of the C-5-epi ABCDE-ring system of rubriflordilactone B has been developed. The present synthesis features a convergent strategy to construct the C-5-<i>epi</i> AB-ring utilizing Mukaiyama–Michael reaction and forge the CDE ring in one step using intramolecular [2 + 2 + 2] cycloaddition of triynes

Total Synthesis of (±)-Przewalskin B

A concise total synthesis of przewalskin B was accomplished from readily available diene 7. Key features of the synthesis involved a Diels–Alder reaction to install the A ring, a Claisen–Johnson rearrangement to establish the spiro-quaternary center, and a ring-closing metathesis (RCM) of a sterically crowded system to construct the cyclic enone moiety

Biomimetic Total Synthesis of Paeoveitol

A highly stereocontrolled synthesis of paeoveitol has been developed in 26% yield, in 7 steps from commercially available materials. The synthetic strategy was inspired primarily by the biogenetic hypothesis and was enabled by hetero-Diels–Alder cycloaddition to construct the target molecular framework