Zhang, P-P.; Yan, Z-M.; Li, Y-H.; Gong, J-X.; Yang, Z. J. Am. Chem. Soc. 2017, 139, 13989-13992.

The enantioselective synthesis of (−)-pavidolide B (1) was achieved in a linear sequence of 10 steps. The key steps are (a) an enantioselective organocatalytic cyclopropanation; (b) a radical-based cascade annulation for the regio- and diastereo-selective synthesis of the highly functionalized lactone 3 bearing the characteristic tricyclic core and seven contiguous stereocenters; (c) a sequential ring-closing metathesis reaction and a RhCl3-catalyzed double bond isomerization to form the seven-membered D ring of (−)-pavidolide B.

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Liu, Q.; Deng, Y.; Smith, A. B. J. Am. Chem. Soc. 2017, 139, 13668–13671.

A convergent total synthesis of (−)-nahuoic acid Ci (Bii) (3), a novel cis-decalin polyketide, has been achieved. Key synthetic transformations include Type II Anion Relay Chemistry (ARC) to construct the polyol chain, a Ti-catalyzed asymmetric Diels−Alder reaction to generate the cis-decalin skeleton, and a late-stage large fragment union exploiting a Micalizio alkoxide-directed alkyne−alkene coupling tactic.

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Tao, D. J.; Slutskyy, Y.; Overman, L. E J. Am. Chem. Soc. 2016, 138, 2186-2189.

The first total synthesis of a chromodorolide diterpenoid is described. The synthesis features a bimolecular radical addition/cyclization/fragmentation cascade that unites butenolide and trans-hydrindane fragments while fashioning two C−C bonds and stereoselectively forming three of the ten contiguous stereocenters of chromodorolide B.

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Hu, P.; Synder, S. A. J. Am. Chem. Soc. 2017, 139, 5007-5010.

A rare element of high strain in molecules of natural origin is a 1,2-trans fusion of 5-membered rings within a [3.3.0]-bicycle, a motif present in (−)-presilphiperfolan-8-ol. This molecule also possesses a 1,3-trans stereochemical arrangement of substituents on one of its 5-membered rings, a pattern shared by a number of other terpenes. Herein, we disclose the first total synthesis of this highly strained target in 13 steps. The key operation is a Pd-catalyzed tandem cyclization that directly establishes the requisite 1,3-trans stereochemical arrangement on one ring while concurrently setting the stage for the controlled generation of the highly strained 1,2-trans ring fusion of the final architecture.

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