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Structurally, they can be described as hybrids of terpenoids, amino acids, and saccharides, and share a characteristic highly strained <jats:italic>anti<\/jats:italic>\u2010<jats:italic>syn<\/jats:italic>\u2010<jats:italic>anti<\/jats:italic>\u2010fused perhydrophenanthrene terpenoid scaffold (ABC\u2010ring system) with two quaternary asymmetric carbon atoms. A unified and stereoselective total synthesis of all four brasilicardins has been designed based on the strategic use of an intramolecular conjugate addition. The ABC\u2010ring system was initially constructed with high stereocontrol by novel intramolecular conjugate additions of Weinreb amides and in situ generated (<jats:italic>Z<\/jats:italic>)\u2010vinyl copper species. The late\u2010stage common intermediate was subjected to stereoselective installation of the amino acid component, followed by introduction of the saccharide unit via glycosylation to accomplish the total synthesis of brasilicardins\u2005A\u2013D. 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