Table 2.

Synthetic features of the total syntheses covered in this review.

Cyclization Method	Group	Synthetic Features
RCM	Kotake (Section 2.2.1)	✓First total synthesis of pladienolide natural products ✓Confirmation of the absolute configuration of pladienolides ✓Reagents-controlled stereoselective reactions
	Ghosh (Section 2.2.2)	✓Convergent and scalable synthesis of pladienolides ✓Convergency enabling convenient access to various derivatives
	Burkart (Section 2.2.3)	✓First total synthesis and structure confirmation of FD-895 ✓Stereodivergent synthesis of side chains to confirm the absolute structure ✓First synthetic approach utilizing cross-coupling to append the side chain unit
	Chandrasekhar (Section 2.2.4)	✓Synthetic flexibility provides side-chain truncated analogs ✓Side-chain truncated analogs prove the importance of the macrocyclic core
	Keaney (Section 2.2.5)	✓Industrial-friendly and cost-effective synthetic approach ✓Chemoselective allylic oxidation to generate C-7 hydroxy group ✓User-friendly Suzuki coupling reaction for the introduction of side chains
	Krische (Section 2.2.6)	✓The shortest total synthesis of pladienolide B ✓Metal-mediated asymmetric dehydrogenative C-C coupling ✓Catalyst-oriented asymmetric synthesis maximizing synthetic convergence
Macro-lactonization	Skaanderup (Section 2.3.1)	✓First synthetic example of the enantiomer of pladienolide B ✓Cross-metathesis–macrolactonization sequence employed ✓The use of Yamaguchi reagent for macrolactonizations
	Maier (Section 2.3.2)	✓The use of commercially available chiral substance at the initial stage ✓HWE olefination–macrolactonization sequence employed ✓Employment of Shiina-type macrolactonization condition
	Rhoades–O’Malley–Wang (Section 2.3.3)	✓The shortest total synthesis of H3B-8800, pladienolide A and B ✓Heck coupling–macrolactonzation sequence employed ✓Thermal macrolactonization conducted in the absence of coupling reagents