An account of the reasoning and reduction to practice of a highly convergent total stereospecific synthesis of calicheamicin gamma(1)(I) (1) is provided. The key finding was the use of a very mild promoter system (silver triflate and 4 Angstrom molecular sieves in methylene chloride) to allow for coupling of trichloroacetimidate 21 with advanced calicheamicinone-like accepters (see 17 and 18). Glycosidation with 17 affords a 3:1 ratio of equatorial to axial glycosides. The use of 18 seems to afford only the equatorial beta-glycoside. Remarkably, use of the enantiomer of 17 as the acceptor gave an 18:1 ratio of axial to equatorial product.